ZA200909096B - Ethynylindole compounds - Google Patents
Ethynylindole compounds Download PDFInfo
- Publication number
- ZA200909096B ZA200909096B ZA200909096A ZA200909096A ZA200909096B ZA 200909096 B ZA200909096 B ZA 200909096B ZA 200909096 A ZA200909096 A ZA 200909096A ZA 200909096 A ZA200909096 A ZA 200909096A ZA 200909096 B ZA200909096 B ZA 200909096B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- compound
- ethynyl
- indole
- acid
- Prior art date
Links
- VYWBXQOYASJNLB-UHFFFAOYSA-N 2-ethynyl-1h-indole Chemical class C1=CC=C2NC(C#C)=CC2=C1 VYWBXQOYASJNLB-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 309
- 239000002253 acid Substances 0.000 claims description 83
- -1 3- carboxypropyl group Chemical group 0.000 claims description 73
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 52
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 48
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 38
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000009472 formulation Methods 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 19
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 17
- 229940002612 prodrug Drugs 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- YWFJJZNSTFOQLJ-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-7-[2-[4-[4-(4-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=CC=C(F)C=C1C YWFJJZNSTFOQLJ-UHFFFAOYSA-N 0.000 claims description 2
- ZSIOUYAJBOECNZ-UHFFFAOYSA-N 2-[1-[[1-(carboxymethyl)-7-[2-[4-[4-(3-fluoro-2-methylphenyl)butoxy]phenyl]ethynyl]-2-methylindol-3-yl]methyl]cyclopropyl]acetic acid Chemical compound C12=CC=CC(C#CC=3C=CC(OCCCCC=4C(=C(F)C=CC=4)C)=CC=3)=C2N(CC(O)=O)C(C)=C1CC1(CC(O)=O)CC1 ZSIOUYAJBOECNZ-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 213
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 186
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 162
- 238000004809 thin layer chromatography Methods 0.000 description 91
- 238000005160 1H NMR spectroscopy Methods 0.000 description 88
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- 230000002829 reductive effect Effects 0.000 description 56
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 55
- 239000011541 reaction mixture Substances 0.000 description 52
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
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- 238000003756 stirring Methods 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 40
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
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- 101150041968 CDC13 gene Proteins 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 27
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
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- 239000013078 crystal Substances 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- HOXJOAWSVADHMC-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-4-fluoro-2-methyl-7-[2-[4-[4-(2,3,4,6-tetrafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=C(F)C=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C=C(F)C(F)=C1F HOXJOAWSVADHMC-UHFFFAOYSA-N 0.000 description 14
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- 229910000024 caesium carbonate Inorganic materials 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000001228 spectrum Methods 0.000 description 13
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002441 X-ray diffraction Methods 0.000 description 12
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- 206010006482 Bronchospasm Diseases 0.000 description 10
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- PASVIKSOGNJXIL-UHFFFAOYSA-N (2-bromo-5-fluorophenyl)hydrazine Chemical compound NNC1=CC(F)=CC=C1Br PASVIKSOGNJXIL-UHFFFAOYSA-N 0.000 description 9
- ZWMQVBSLMQSMDH-UHFFFAOYSA-N (2-bromophenyl)hydrazine Chemical compound NNC1=CC=CC=C1Br ZWMQVBSLMQSMDH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- XBPOBCXHALHJFP-UHFFFAOYSA-N ethyl 4-bromobutanoate Chemical compound CCOC(=O)CCCBr XBPOBCXHALHJFP-UHFFFAOYSA-N 0.000 description 8
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- HLPSHXIVNYPKND-UHFFFAOYSA-N 4-[1-(3-carboxypropyl)-2-methyl-7-[2-[4-[4-(2,3,4,5,6-pentafluorophenyl)butoxy]phenyl]ethynyl]indol-3-yl]butanoic acid Chemical compound C=12N(CCCC(O)=O)C(C)=C(CCCC(O)=O)C2=CC=CC=1C#CC(C=C1)=CC=C1OCCCCC1=C(F)C(F)=C(F)C(F)=C1F HLPSHXIVNYPKND-UHFFFAOYSA-N 0.000 description 7
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 description 1
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- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
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- KFVSLSTULZVNPG-UHFFFAOYSA-N terbutaline sulfate Chemical compound [O-]S([O-])(=O)=O.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1.CC(C)(C)[NH2+]CC(O)C1=CC(O)=CC(O)=C1 KFVSLSTULZVNPG-UHFFFAOYSA-N 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- HTJXMOGUGMSZOG-UHFFFAOYSA-N tiaramide Chemical compound C1CN(CCO)CCN1C(=O)CN1C(=O)SC2=CC=C(Cl)C=C21 HTJXMOGUGMSZOG-UHFFFAOYSA-N 0.000 description 1
- 229950010302 tiaramide Drugs 0.000 description 1
- PFENFDGYVLAFBR-UHFFFAOYSA-N tinoridine Chemical compound C1CC=2C(C(=O)OCC)=C(N)SC=2CN1CC1=CC=CC=C1 PFENFDGYVLAFBR-UHFFFAOYSA-N 0.000 description 1
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- MWYHLEQJTQJHSS-UHFFFAOYSA-N tomelukast Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCCC1=NNN=N1 MWYHLEQJTQJHSS-UHFFFAOYSA-N 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 1
- 229960001593 triprolidine hydrochloride Drugs 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008325815 | 2008-12-22 |
Publications (1)
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|---|---|
| ZA200909096B true ZA200909096B (en) | 2010-09-29 |
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|---|---|---|---|
| ZA200909096A ZA200909096B (en) | 2008-12-22 | 2009-12-21 | Ethynylindole compounds |
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| Country | Link |
|---|---|
| US (1) | US8115014B2 (ru) |
| EP (1) | EP2206698B1 (ru) |
| JP (2) | JP5012884B2 (ru) |
| KR (1) | KR101464778B1 (ru) |
| CN (1) | CN101759628B (ru) |
| AU (1) | AU2009250960C1 (ru) |
| BR (1) | BRPI0905601A2 (ru) |
| CA (1) | CA2688614C (ru) |
| DK (1) | DK2206698T3 (ru) |
| ES (1) | ES2387185T3 (ru) |
| IL (1) | IL202869A (ru) |
| MX (1) | MX2009013926A (ru) |
| NZ (1) | NZ582208A (ru) |
| PL (1) | PL2206698T3 (ru) |
| PT (1) | PT2206698E (ru) |
| RU (1) | RU2505531C2 (ru) |
| TW (1) | TWI469965B (ru) |
| ZA (1) | ZA200909096B (ru) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| TW201229038A (en) * | 2010-06-21 | 2012-07-16 | Ono Pharmaceutical Co | Novel crystalline form of 4,4'-[4-fluoro-7-({4-[4-(3-fluoro-2-methylpheny)butoxy]phenyl}ethynyl)-2-methyl-1h-indole-1,3-diyl]dibutanoic acid, 4,4'-[2-methyl-7-({4-[4-(pentafluorophenyl)butoxy]phenyl}ethynyl)-1h-indole-1,3-diyl]dibutanoic acid |
| KR101171790B1 (ko) | 2010-07-30 | 2012-08-13 | 현대자동차주식회사 | 인출식 자전거 캐리어 |
| LT2658844T (lt) | 2010-12-28 | 2017-02-10 | Sanofi | Nauji pirimidino dariniai, jų gamyba ir jų farmacinis panaudojimas kaip akt (pkb) fosforilinimo slopiklių |
| EP2537866A1 (en) * | 2011-06-21 | 2012-12-26 | Serumwerk Bernburg AG | Hydroxyethyl starch derivatives, method for manufacturing the same and therapeutical uses thereof |
| CN103893146A (zh) * | 2012-12-25 | 2014-07-02 | 天津药物研究院 | 含福多司坦缓释剂型 |
| US11427591B2 (en) * | 2018-10-17 | 2022-08-30 | Insilico Medicine Ip Limited | Kinase inhibitors |
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| BE555319A (ru) | 1956-03-21 | 1900-01-01 | ||
| US3095355A (en) | 1961-10-12 | 1963-06-25 | Revlon | Aerosol composition |
| JPH01192476A (ja) | 1988-01-25 | 1989-08-02 | Kawasaki Steel Corp | 溶接鋼管の製造方法 |
| US5137910A (en) | 1989-05-05 | 1992-08-11 | C.D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
| US5229413A (en) | 1989-05-05 | 1993-07-20 | G. D. Searle & Co. | Compositions containing indole-2-carboxylate compounds for treatment of CNS disorders |
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-
2009
- 2009-12-10 TW TW98142268A patent/TWI469965B/zh not_active IP Right Cessation
- 2009-12-15 CA CA2688614A patent/CA2688614C/en not_active Expired - Fee Related
- 2009-12-15 AU AU2009250960A patent/AU2009250960C1/en not_active Ceased
- 2009-12-17 MX MX2009013926A patent/MX2009013926A/es active IP Right Grant
- 2009-12-21 RU RU2009147506/04A patent/RU2505531C2/ru not_active IP Right Cessation
- 2009-12-21 ZA ZA200909096A patent/ZA200909096B/en unknown
- 2009-12-21 BR BRPI0905601-7A patent/BRPI0905601A2/pt not_active IP Right Cessation
- 2009-12-21 PL PL09180244T patent/PL2206698T3/pl unknown
- 2009-12-21 EP EP09180244A patent/EP2206698B1/en not_active Not-in-force
- 2009-12-21 DK DK09180244.7T patent/DK2206698T3/da active
- 2009-12-21 JP JP2009289494A patent/JP5012884B2/ja active Active
- 2009-12-21 KR KR1020090128213A patent/KR101464778B1/ko not_active IP Right Cessation
- 2009-12-21 ES ES09180244T patent/ES2387185T3/es active Active
- 2009-12-21 CN CN2009102608650A patent/CN101759628B/zh not_active Expired - Fee Related
- 2009-12-21 IL IL202869A patent/IL202869A/en not_active IP Right Cessation
- 2009-12-21 PT PT09180244T patent/PT2206698E/pt unknown
- 2009-12-21 NZ NZ582208A patent/NZ582208A/en not_active IP Right Cessation
- 2009-12-22 US US12/644,378 patent/US8115014B2/en not_active Expired - Fee Related
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2012
- 2012-03-07 JP JP2012050217A patent/JP2012144546A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| US8115014B2 (en) | 2012-02-14 |
| BRPI0905601A2 (pt) | 2012-05-02 |
| AU2009250960A1 (en) | 2010-07-08 |
| AU2009250960C1 (en) | 2014-01-23 |
| ES2387185T3 (es) | 2012-09-17 |
| MX2009013926A (es) | 2010-06-22 |
| RU2009147506A (ru) | 2011-06-27 |
| CN101759628B (zh) | 2013-02-27 |
| AU2009250960B2 (en) | 2013-09-05 |
| CA2688614A1 (en) | 2010-06-22 |
| NZ582208A (en) | 2011-05-27 |
| EP2206698A1 (en) | 2010-07-14 |
| PT2206698E (pt) | 2012-08-03 |
| JP2010168359A (ja) | 2010-08-05 |
| US20100160647A1 (en) | 2010-06-24 |
| JP2012144546A (ja) | 2012-08-02 |
| CA2688614C (en) | 2015-01-06 |
| TWI469965B (zh) | 2015-01-21 |
| JP5012884B2 (ja) | 2012-08-29 |
| EP2206698B1 (en) | 2012-07-18 |
| PL2206698T3 (pl) | 2012-12-31 |
| DK2206698T3 (da) | 2012-08-27 |
| TW201026664A (en) | 2010-07-16 |
| IL202869A (en) | 2015-02-26 |
| CN101759628A (zh) | 2010-06-30 |
| KR20100074036A (ko) | 2010-07-01 |
| KR101464778B1 (ko) | 2014-11-24 |
| RU2505531C2 (ru) | 2014-01-27 |
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