SK63197A3 - Heterocyclic antagonists of bradykinin containing sulphur, preparation method thereof and drugs containing the same - Google Patents
Heterocyclic antagonists of bradykinin containing sulphur, preparation method thereof and drugs containing the same Download PDFInfo
- Publication number
- SK63197A3 SK63197A3 SK631-97A SK63197A SK63197A3 SK 63197 A3 SK63197 A3 SK 63197A3 SK 63197 A SK63197 A SK 63197A SK 63197 A3 SK63197 A3 SK 63197A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- alkyl
- group
- carbon atoms
- Prior art date
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000003814 drug Substances 0.000 title claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 title claims 2
- 239000005864 Sulphur Substances 0.000 title abstract 2
- 101800004538 Bradykinin Proteins 0.000 title description 18
- QXZGBUJJYSLZLT-UHFFFAOYSA-N H-Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg-OH Natural products NC(N)=NCCCC(N)C(=O)N1CCCC1C(=O)N1C(C(=O)NCC(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CO)C(=O)N2C(CCC2)C(=O)NC(CC=2C=CC=CC=2)C(=O)NC(CCCN=C(N)N)C(O)=O)CCC1 QXZGBUJJYSLZLT-UHFFFAOYSA-N 0.000 title description 18
- QXZGBUJJYSLZLT-FDISYFBBSA-N bradykinin Chemical compound NC(=N)NCCC[C@H](N)C(=O)N1CCC[C@H]1C(=O)N1[C@H](C(=O)NCC(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CO)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)CCC1 QXZGBUJJYSLZLT-FDISYFBBSA-N 0.000 title description 18
- 238000002360 preparation method Methods 0.000 title description 15
- 239000005557 antagonist Substances 0.000 title description 5
- 229940079593 drug Drugs 0.000 title description 2
- 102100035792 Kininogen-1 Human genes 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 35
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims abstract description 7
- 235000004279 alanine Nutrition 0.000 claims abstract description 7
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
- 229930182817 methionine Natural products 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims abstract description 3
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 120
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 229910001868 water Inorganic materials 0.000 claims description 20
- 239000012442 inert solvent Substances 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 5
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 229960000310 isoleucine Drugs 0.000 claims description 5
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 239000011734 sodium Chemical group 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229940124277 aminobutyric acid Drugs 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 4
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 3
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 3
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- 239000001569 carbon dioxide Substances 0.000 claims description 3
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- 235000018417 cysteine Nutrition 0.000 claims description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000004474 valine Substances 0.000 claims description 3
- BVAUMRCGVHUWOZ-ZETCQYMHSA-N (2s)-2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1CCCCC1 BVAUMRCGVHUWOZ-ZETCQYMHSA-N 0.000 claims description 2
- NYCRCTMDYITATC-UHFFFAOYSA-N 2-fluorophenylalanine Chemical compound OC(=O)C(N)CC1=CC=CC=C1F NYCRCTMDYITATC-UHFFFAOYSA-N 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- AQTFKGDWFRRIHR-UHFFFAOYSA-L 3-[18-(2-carboxylatoethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoate;cobalt(2+);hydron Chemical group [Co+2].[N-]1C(C=C2C(=C(C)C(C=C3C(=C(C)C(=C4)[N-]3)C=C)=N2)C=C)=C(C)C(CCC(O)=O)=C1C=C1C(CCC(O)=O)=C(C)C4=N1 AQTFKGDWFRRIHR-UHFFFAOYSA-L 0.000 claims description 2
- JJDJLFDGCUYZMN-QMMMGPOBSA-N 3-chloro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(Cl)=C1 JJDJLFDGCUYZMN-QMMMGPOBSA-N 0.000 claims description 2
- XWHHYOYVRVGJJY-QMMMGPOBSA-N 4-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(F)C=C1 XWHHYOYVRVGJJY-QMMMGPOBSA-N 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- NIGWMJHCCYYCSF-UHFFFAOYSA-N Fenclonine Chemical compound OC(=O)C(N)CC1=CC=C(Cl)C=C1 NIGWMJHCCYYCSF-UHFFFAOYSA-N 0.000 claims description 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 2
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- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
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- 229910052792 caesium Chemical group 0.000 claims description 2
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- VWHRYODZTDMVSS-QMMMGPOBSA-N m-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC(F)=C1 VWHRYODZTDMVSS-QMMMGPOBSA-N 0.000 claims description 2
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- 238000007363 ring formation reaction Methods 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- CVZZNRXMDCOHBG-UHFFFAOYSA-N 2-azaniumyl-3-(2-chlorophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=CC=C1Cl CVZZNRXMDCOHBG-UHFFFAOYSA-N 0.000 claims 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims 1
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 1
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- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- UYRCOTSOPWOSJK-JXTBTVDRSA-N bradykinin antagonist Chemical class C1C2=CC=CC=C2CC1[C@@H](NC(=O)C(CO)NC(=O)C(NC(=O)CNC(=O)[C@H]1N(C[C@H](O)C1)C(=O)C1N(CCC1)C(=O)C(CCCNC(N)=N)NC(=O)[C@@H](CCCNC(N)=N)NC(=N)CCCCCCC(=N)N[C@H](CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(=O)N1C(CCC1)C(=O)N1[C@@H](C[C@@H](O)C1)C(=O)NCC(=O)NC(C1CC2=CC=CC=C2C1)C(=O)NC(CO)C(=O)N[C@H](C1CC2=CC=CC=C2C1)C(=O)N1C2CCCCC2CC1C(=O)NC(CCCNC(N)=N)C(O)=O)C1CC2=CC=CC=C2C1)C(=O)N1C2CCCCC2CC1C(=O)NC(CCCNC(=N)N)C(O)=O UYRCOTSOPWOSJK-JXTBTVDRSA-N 0.000 abstract description 2
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19620508A DE19620508A1 (de) | 1996-05-22 | 1996-05-22 | Schwefelenthaltende heterocyclische Bradykinin-Antagonisten, Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK63197A3 true SK63197A3 (en) | 1997-12-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK631-97A SK63197A3 (en) | 1996-05-22 | 1997-05-20 | Heterocyclic antagonists of bradykinin containing sulphur, preparation method thereof and drugs containing the same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5834500A (ko) |
| EP (1) | EP0808838B1 (ko) |
| JP (1) | JP4125803B2 (ko) |
| KR (1) | KR970074781A (ko) |
| CN (1) | CN1169992A (ko) |
| AT (1) | ATE252567T1 (ko) |
| AU (1) | AU2351097A (ko) |
| BR (1) | BR9703370A (ko) |
| CA (1) | CA2205785A1 (ko) |
| CZ (1) | CZ154797A3 (ko) |
| DE (2) | DE19620508A1 (ko) |
| ES (1) | ES2205086T3 (ko) |
| HR (1) | HRP970279A2 (ko) |
| HU (1) | HUP9700914A3 (ko) |
| ID (1) | ID16952A (ko) |
| IL (1) | IL120863A0 (ko) |
| NO (1) | NO972312L (ko) |
| PL (1) | PL320105A1 (ko) |
| SK (1) | SK63197A3 (ko) |
| TR (1) | TR199700391A2 (ko) |
| ZA (1) | ZA974416B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7202363B2 (en) * | 2003-07-24 | 2007-04-10 | Abbott Laboratories | Thienopyridine and furopyridine kinase inhibitors |
| AU2006228957A1 (en) * | 2005-04-01 | 2006-10-05 | Methylgene Inc. | Inhibitors of histone deacetylase |
| AU2009322270B2 (en) | 2008-12-05 | 2014-12-18 | Abbvie Bahamas Ltd | Thieno [3, 2-c] pyridine derivatives as kinase inhibitors for use in the treatment of cancer |
| WO2013012909A1 (en) | 2011-07-20 | 2013-01-24 | Abbott Laboratories | Kinase inhibitor with improved aqueous solubility |
| HRP20220331T1 (hr) | 2018-03-08 | 2022-05-13 | Incyte Corporation | Spojevi aminopirazin diola kao inhibitori pi3k-y |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
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|---|---|---|---|---|
| IE64995B1 (en) * | 1987-07-14 | 1995-09-20 | Warner Lambert Co | Novel benzothiophenes having antiallergic activity and both novel and other selected benzothiophenes having activity for treating acute respiratory distress syndrome |
| US4863923A (en) * | 1988-07-01 | 1989-09-05 | Eli Lilly And Company | Method of inhibiting superoxide release |
| EP0534505B1 (en) * | 1989-07-06 | 1998-12-09 | Toyota Jidosha Kabushiki Kaisha | Laser deposition method |
| US5212182A (en) * | 1990-10-03 | 1993-05-18 | American Home Products Corpooration | Substituted quinolinyl- and naphthalenylbenzamides or benzylamines and related compounds useful as analgesics |
| GB9122098D0 (en) * | 1991-10-17 | 1991-11-27 | Ici Plc | Fungicides |
| US5438064A (en) * | 1991-12-23 | 1995-08-01 | American Home Products Corporation | Derivatives of 4-anilinoquinoline-3-carboxamide as analgesic agents |
| AU686115B2 (en) * | 1992-11-02 | 1998-02-05 | Fujisawa Pharmaceutical Co., Ltd. | Imidazo (I,2-a) pyridine derivatives as bradykinin antagonists, pharmaceuticals and processes for their preparation |
| AU680870B2 (en) * | 1993-04-28 | 1997-08-14 | Astellas Pharma Inc. | New heterocyclic compounds |
| GB9317949D0 (en) * | 1993-08-28 | 1993-10-13 | Stevens Malcolm F G | Benzothiazole compounds |
| US5545641A (en) * | 1994-10-20 | 1996-08-13 | Eli Lilly And Company | Methods of inhibiting physiological conditions associated with an excess of bradykinin |
| WO1996012488A1 (en) * | 1994-10-20 | 1996-05-02 | Eli Lilly And Company | Bicyclic bradykinin receptor antagonists |
| KR970707098A (ko) * | 1994-10-27 | 1997-12-01 | 후지야마 아키라 | 브라디키닌 길항제로서 피리도피리미돈, 퀴놀린 및 융합된 N-헤테로사이클(Pyridopyrimidones, quinolines and fused N-heterocycles as bradykinin antagonists) |
-
1996
- 1996-05-22 DE DE19620508A patent/DE19620508A1/de not_active Withdrawn
-
1997
- 1997-05-09 EP EP97107623A patent/EP0808838B1/de not_active Expired - Lifetime
- 1997-05-09 ES ES97107623T patent/ES2205086T3/es not_active Expired - Lifetime
- 1997-05-09 AT AT97107623T patent/ATE252567T1/de not_active IP Right Cessation
- 1997-05-09 DE DE59710874T patent/DE59710874D1/de not_active Expired - Lifetime
- 1997-05-16 US US08/858,077 patent/US5834500A/en not_active Expired - Lifetime
- 1997-05-20 CZ CZ971547A patent/CZ154797A3/cs unknown
- 1997-05-20 AU AU23510/97A patent/AU2351097A/en not_active Abandoned
- 1997-05-20 IL IL12086397A patent/IL120863A0/xx unknown
- 1997-05-20 SK SK631-97A patent/SK63197A3/sk unknown
- 1997-05-20 TR TR97/00391A patent/TR199700391A2/xx unknown
- 1997-05-20 HU HU9700914A patent/HUP9700914A3/hu unknown
- 1997-05-20 CN CN97113120A patent/CN1169992A/zh active Pending
- 1997-05-21 JP JP13116197A patent/JP4125803B2/ja not_active Expired - Fee Related
- 1997-05-21 PL PL97320105A patent/PL320105A1/xx unknown
- 1997-05-21 CA CA002205785A patent/CA2205785A1/en not_active Abandoned
- 1997-05-21 NO NO972312A patent/NO972312L/no unknown
- 1997-05-21 ID IDP971699A patent/ID16952A/id unknown
- 1997-05-21 HR HR19620508.5A patent/HRP970279A2/xx not_active Application Discontinuation
- 1997-05-21 ZA ZA9704416A patent/ZA974416B/xx unknown
- 1997-05-22 KR KR1019970019898A patent/KR970074781A/ko not_active Application Discontinuation
- 1997-05-22 BR BR9703370A patent/BR9703370A/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0808838A1 (de) | 1997-11-26 |
| KR970074781A (ko) | 1997-12-10 |
| CA2205785A1 (en) | 1997-11-22 |
| HUP9700914A3 (en) | 1999-05-28 |
| TR199700391A2 (xx) | 1997-12-21 |
| CN1169992A (zh) | 1998-01-14 |
| NO972312D0 (no) | 1997-05-21 |
| US5834500A (en) | 1998-11-10 |
| MX9703724A (es) | 1998-06-28 |
| ZA974416B (en) | 1997-11-24 |
| CZ154797A3 (en) | 1997-12-17 |
| NO972312L (no) | 1997-11-24 |
| ID16952A (id) | 1997-11-27 |
| ES2205086T3 (es) | 2004-05-01 |
| HU9700914D0 (en) | 1997-07-28 |
| EP0808838B1 (de) | 2003-10-22 |
| DE19620508A1 (de) | 1997-11-27 |
| ATE252567T1 (de) | 2003-11-15 |
| HRP970279A2 (en) | 1998-04-30 |
| IL120863A0 (en) | 1997-09-30 |
| PL320105A1 (en) | 1997-11-24 |
| DE59710874D1 (de) | 2003-11-27 |
| HUP9700914A2 (hu) | 1998-11-30 |
| JPH1067762A (ja) | 1998-03-10 |
| AU2351097A (en) | 1997-11-27 |
| BR9703370A (pt) | 1998-09-22 |
| JP4125803B2 (ja) | 2008-07-30 |
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