CA2655723C - Compositions and methods of making a photoactive agent - Google Patents
Compositions and methods of making a photoactive agent Download PDFInfo
- Publication number
- CA2655723C CA2655723C CA2655723A CA2655723A CA2655723C CA 2655723 C CA2655723 C CA 2655723C CA 2655723 A CA2655723 A CA 2655723A CA 2655723 A CA2655723 A CA 2655723A CA 2655723 C CA2655723 C CA 2655723C
- Authority
- CA
- Canada
- Prior art keywords
- chlorin
- salt
- formula
- combining
- composition
- 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.)
- Active
Links
- 239000000203 mixture Substances 0.000 title claims description 64
- 238000000034 method Methods 0.000 title claims description 60
- 239000000906 photoactive agent Substances 0.000 title description 4
- OYINILBBZAQBEV-UWJYYQICSA-N (17s,18s)-18-(2-carboxyethyl)-20-(carboxymethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18,22,23-tetrahydroporphyrin-2-carboxylic acid Chemical compound N1C2=C(C)C(C=C)=C1C=C(N1)C(C)=C(CC)C1=CC(C(C)=C1C(O)=O)=NC1=C(CC(O)=O)C([C@@H](CCC(O)=O)[C@@H]1C)=NC1=C2 OYINILBBZAQBEV-UWJYYQICSA-N 0.000 claims abstract description 76
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 18
- 238000005859 coupling reaction Methods 0.000 claims abstract description 18
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims description 72
- SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims description 56
- -1 L-aspartyl chlorin e6 Chemical compound 0.000 claims description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 24
- 150000001412 amines Chemical class 0.000 claims description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000012304 carboxyl activating agent Substances 0.000 claims description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 16
- 229960005261 aspartic acid Drugs 0.000 claims description 15
- 239000003153 chemical reaction reagent Substances 0.000 claims description 15
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 13
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 12
- WTWSHHITWMVLBX-DKWTVANSSA-M sodium;(2s)-2-aminobutanedioate;hydron Chemical compound [Na+].[O-]C(=O)[C@@H](N)CC(O)=O WTWSHHITWMVLBX-DKWTVANSSA-M 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 abstract description 58
- 239000011541 reaction mixture Substances 0.000 abstract description 51
- 239000002243 precursor Substances 0.000 abstract description 37
- 238000006243 chemical reaction Methods 0.000 abstract description 33
- 230000004913 activation Effects 0.000 abstract description 21
- 238000000746 purification Methods 0.000 abstract description 12
- 150000008064 anhydrides Chemical class 0.000 abstract description 10
- 229940009098 aspartate Drugs 0.000 abstract 1
- VSEIDZLLWQQJGK-CHOZPQDDSA-N CCC1=C(C)C2=N\C\1=C/C1=C(C)C(C(O)=O)=C(N1)\C(CC(=O)N[C@@H](CC(O)=O)C(O)=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)[C@@H](C)[C@@H]1CCC(O)=O Chemical compound CCC1=C(C)C2=N\C\1=C/C1=C(C)C(C(O)=O)=C(N1)\C(CC(=O)N[C@@H](CC(O)=O)C(O)=O)=C1/N=C(/C=C3\N/C(=C\2)C(C=C)=C3C)[C@@H](C)[C@@H]1CCC(O)=O VSEIDZLLWQQJGK-CHOZPQDDSA-N 0.000 description 51
- 229950010924 talaporfin Drugs 0.000 description 50
- 241000894007 species Species 0.000 description 40
- 239000003795 chemical substances by application Substances 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 238000000926 separation method Methods 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 230000018044 dehydration Effects 0.000 description 8
- 238000006297 dehydration reaction Methods 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 230000001376 precipitating effect Effects 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000002835 absorbance Methods 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 3
- 235000001014 amino acid Nutrition 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000009877 rendering Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 235000003704 aspartic acid Nutrition 0.000 description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000132 electrospray ionisation Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000001115 mace Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 238000001292 planar chromatography Methods 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81776906P | 2006-06-30 | 2006-06-30 | |
| US60/817,769 | 2006-06-30 | ||
| PCT/US2007/015087 WO2008005308A2 (en) | 2006-06-30 | 2007-06-29 | Compositions and methods of making a chlorin e6 derivative as a photoactive agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2655723A1 CA2655723A1 (en) | 2008-01-10 |
| CA2655723C true CA2655723C (en) | 2014-11-18 |
Family
ID=38739490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2655723A Active CA2655723C (en) | 2006-06-30 | 2007-06-29 | Compositions and methods of making a photoactive agent |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8198312B2 (enExample) |
| EP (1) | EP2057169A2 (enExample) |
| JP (1) | JP5323693B2 (enExample) |
| KR (1) | KR101456839B1 (enExample) |
| CN (1) | CN101490057B (enExample) |
| AU (1) | AU2007269784B2 (enExample) |
| CA (1) | CA2655723C (enExample) |
| RU (1) | RU2009102973A (enExample) |
| SG (1) | SG172733A1 (enExample) |
| WO (1) | WO2008005308A2 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN2885311Y (zh) | 2006-01-18 | 2007-04-04 | 郑成福 | 经尿道光动力疗法前列腺治疗仪 |
| US7465312B2 (en) | 2006-05-02 | 2008-12-16 | Green Medical, Inc. | Systems and methods for treating superficial venous malformations like spider veins |
| WO2007130465A2 (en) * | 2006-05-02 | 2007-11-15 | Green Medical, Inc. | Systems and methods for treating superficial venous malformations like spider veins |
| JP5323693B2 (ja) | 2006-06-30 | 2013-10-23 | ライト、サイエンシーズ、オンコロジー、インコーポレイテッド | 光活性剤としてのクロリンｅ６誘導体の組成物およびクロリンｅ６誘導体を製造する方法 |
| CN103030644B (zh) * | 2011-09-30 | 2015-01-14 | 齐鲁制药有限公司 | 一种他拉泊芬及其中间体的制备方法 |
| US10740438B2 (en) | 2012-08-16 | 2020-08-11 | Ginger.io, Inc. | Method and system for characterizing and/or treating poor sleep behavior |
| CN109785972B (zh) | 2012-08-16 | 2023-09-26 | 橙点公司 | 用于对行为和健康变化进行建模的方法 |
| US10741285B2 (en) | 2012-08-16 | 2020-08-11 | Ginger.io, Inc. | Method and system for providing automated conversations |
| US10650920B2 (en) | 2012-08-16 | 2020-05-12 | Ginger.io, Inc. | Method and system for improving care determination |
| US10748645B2 (en) | 2012-08-16 | 2020-08-18 | Ginger.io, Inc. | Method for providing patient indications to an entity |
| US10276260B2 (en) | 2012-08-16 | 2019-04-30 | Ginger.io, Inc. | Method for providing therapy to an individual |
| RU2523380C1 (ru) * | 2013-05-21 | 2014-07-20 | Общество с ограниченной ответственностью "ГЕЛИОХЛОРИН" | Фотосенсибилизатор и способ его получения |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4675338A (en) * | 1984-07-18 | 1987-06-23 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| US4693885A (en) | 1984-07-18 | 1987-09-15 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| US4977177A (en) * | 1985-04-30 | 1990-12-11 | Nippon Petrochemicals Company, Ltd. | Tetrapyrrole polyaminomonocarboxylic acid therapeutic agents |
| US4656186A (en) | 1985-04-30 | 1987-04-07 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| JP3565442B2 (ja) * | 1993-04-22 | 2004-09-15 | 新日本石油化学株式会社 | 哺乳類の関節炎の診断剤および／または治療剤 |
| JP5323693B2 (ja) | 2006-06-30 | 2013-10-23 | ライト、サイエンシーズ、オンコロジー、インコーポレイテッド | 光活性剤としてのクロリンｅ６誘導体の組成物およびクロリンｅ６誘導体を製造する方法 |
-
2007
- 2007-06-29 JP JP2009518280A patent/JP5323693B2/ja not_active Expired - Fee Related
- 2007-06-29 KR KR1020097002051A patent/KR101456839B1/ko not_active Expired - Fee Related
- 2007-06-29 AU AU2007269784A patent/AU2007269784B2/en not_active Ceased
- 2007-06-29 CA CA2655723A patent/CA2655723C/en active Active
- 2007-06-29 US US11/772,024 patent/US8198312B2/en active Active
- 2007-06-29 CN CN2007800274940A patent/CN101490057B/zh not_active Expired - Fee Related
- 2007-06-29 WO PCT/US2007/015087 patent/WO2008005308A2/en not_active Ceased
- 2007-06-29 RU RU2009102973/04A patent/RU2009102973A/ru unknown
- 2007-06-29 EP EP07810026A patent/EP2057169A2/en not_active Ceased
- 2007-06-29 SG SG2011046810A patent/SG172733A1/en unknown
-
2010
- 2010-11-01 US US12/917,353 patent/US8063203B2/en active Active
-
2012
- 2012-05-16 US US13/473,395 patent/US8822677B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20080021210A1 (en) | 2008-01-24 |
| CA2655723A1 (en) | 2008-01-10 |
| WO2008005308A3 (en) | 2008-03-06 |
| JP5323693B2 (ja) | 2013-10-23 |
| JP2009542672A (ja) | 2009-12-03 |
| AU2007269784A1 (en) | 2008-01-10 |
| US8198312B2 (en) | 2012-06-12 |
| CN101490057B (zh) | 2013-02-27 |
| US8063203B2 (en) | 2011-11-22 |
| US20130281689A1 (en) | 2013-10-24 |
| RU2009102973A (ru) | 2010-08-10 |
| WO2008005308A2 (en) | 2008-01-10 |
| KR20090033463A (ko) | 2009-04-03 |
| US8822677B2 (en) | 2014-09-02 |
| KR101456839B1 (ko) | 2014-11-03 |
| SG172733A1 (en) | 2011-07-28 |
| US20110105745A1 (en) | 2011-05-05 |
| CN101490057A (zh) | 2009-07-22 |
| AU2007269784B2 (en) | 2012-07-05 |
| EP2057169A2 (en) | 2009-05-13 |
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