JP5323693B2 - 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 - Google Patents
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 Download PDFInfo
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- JP5323693B2 JP5323693B2 JP2009518280A JP2009518280A JP5323693B2 JP 5323693 B2 JP5323693 B2 JP 5323693B2 JP 2009518280 A JP2009518280 A JP 2009518280A JP 2009518280 A JP2009518280 A JP 2009518280A JP 5323693 B2 JP5323693 B2 JP 5323693B2
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- Prior art keywords
- chlorin
- formula
- salt
- reaction mixture
- anhydride
- 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 - Fee Related
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- 239000000203 mixture Substances 0.000 title claims description 99
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- 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 group 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 title 2
- 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 245
- 150000003839 salts Chemical class 0.000 claims description 117
- 238000000034 method Methods 0.000 claims description 113
- 239000011541 reaction mixture Substances 0.000 claims description 91
- 150000008064 anhydrides Chemical class 0.000 claims description 72
- 239000002243 precursor Substances 0.000 claims description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 43
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 33
- 150000001412 amines Chemical class 0.000 claims description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 22
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims description 21
- 150000001718 carbodiimides Chemical class 0.000 claims description 21
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- 238000000926 separation method Methods 0.000 claims description 17
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 claims description 16
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 claims description 16
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 15
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- -1 cyclic anhydride Chemical class 0.000 claims description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 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 8
- 238000001914 filtration Methods 0.000 claims description 7
- 239000000377 silicon dioxide Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
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- 238000001556 precipitation Methods 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 description 83
- 239000000543 intermediate Substances 0.000 description 69
- 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 61
- 229950010924 talaporfin Drugs 0.000 description 60
- 241000894007 species Species 0.000 description 54
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- 239000012304 carboxyl activating agent Substances 0.000 description 16
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- 238000004128 high performance liquid chromatography Methods 0.000 description 13
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- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
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- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- NCVQSYGZKXPLLC-KUNYHPRLSA-N CCC1=C(C)C(/C=C(/C(C=C)=C2C)\N/C2=C\C([C@@H](C)C23C(CC(O)=O)C2)=N/C3=C2/CC(OC3=O)=O)=N/C1=C\c1c(C)c3c2[nH]1 Chemical compound CCC1=C(C)C(/C=C(/C(C=C)=C2C)\N/C2=C\C([C@@H](C)C23C(CC(O)=O)C2)=N/C3=C2/CC(OC3=O)=O)=N/C1=C\c1c(C)c3c2[nH]1 NCVQSYGZKXPLLC-KUNYHPRLSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 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
- 235000003704 aspartic acid Nutrition 0.000 description 3
- 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 3
- 201000011510 cancer Diseases 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 0 C[C@](C(C=*)C(N1)=C[C@@](C2)C(C)=C(CO)C2=C2)C1=CC([C@@](C)[C@]13C(C*)C1)=NC3=C(CC(O)=O)C1=C(*)C(C)[C@]2N1 Chemical compound C[C@](C(C=*)C(N1)=C[C@@](C2)C(C)=C(CO)C2=C2)C1=CC([C@@](C)[C@]13C(C*)C1)=NC3=C(CC(O)=O)C1=C(*)C(C)[C@]2N1 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 125000000570 L-alpha-aspartyl group Chemical group [H]OC(=O)C([H])([H])[C@]([H])(N([H])[H])C(*)=O 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000004035 chlorins Chemical class 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
- 238000001035 drying Methods 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
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000002186 photoactivation Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000243 solution 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
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-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
- OFHGNTCTXUMNNS-WHNFKYNOSA-N CC[C@@H](C12C(CC(O)=O)C1)C(/C=C(/C(C)=C1C=C)\N/C1=C\C(C(C)=C1CC)=N/C1=C\c([nH]1)c3C)=N/C2=C(/CC(O2)=O)\c1c3C2=O Chemical compound CC[C@@H](C12C(CC(O)=O)C1)C(/C=C(/C(C)=C1C=C)\N/C1=C\C(C(C)=C1CC)=N/C1=C\c([nH]1)c3C)=N/C2=C(/CC(O2)=O)\c1c3C2=O OFHGNTCTXUMNNS-WHNFKYNOSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 235000009421 Myristica fragrans Nutrition 0.000 description 1
- 206010053648 Vascular occlusion Diseases 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
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- 230000030833 cell death Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-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
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- 238000007429 general method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 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
- 230000007774 longterm Effects 0.000 description 1
- 239000001115 mace Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 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
- 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
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- 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
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (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)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2009542672A JP2009542672A (ja) | 2009-12-03 |
| JP2009542672A5 JP2009542672A5 (enExample) | 2011-07-28 |
| JP5323693B2 true JP5323693B2 (ja) | 2013-10-23 |
Family
ID=38739490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518280A Expired - Fee Related JP5323693B2 (ja) | 2006-06-30 | 2007-06-29 | 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 |
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 |
| EP2057169A2 (en) | 2006-06-30 | 2009-05-13 | Light Sciences Oncology, Inc. | Compositions and methods of making a chlorin e6 derivative as a photoactive agent |
| 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 |
| US10741285B2 (en) | 2012-08-16 | 2020-08-11 | Ginger.io, Inc. | Method and system for providing automated conversations |
| US10740438B2 (en) | 2012-08-16 | 2020-08-11 | Ginger.io, Inc. | Method and system for characterizing and/or treating poor sleep behavior |
| US10650920B2 (en) | 2012-08-16 | 2020-05-12 | Ginger.io, Inc. | Method and system for improving care determination |
| WO2014028888A2 (en) | 2012-08-16 | 2014-02-20 | Ginger.io, Inc. | Method for modeling behavior and health changes |
| US10276260B2 (en) | 2012-08-16 | 2019-04-30 | Ginger.io, Inc. | Method for providing therapy to an individual |
| US10748645B2 (en) | 2012-08-16 | 2020-08-18 | Ginger.io, Inc. | Method for providing patient indications to an entity |
| RU2523380C1 (ru) * | 2013-05-21 | 2014-07-20 | Общество с ограниченной ответственностью "ГЕЛИОХЛОРИН" | Фотосенсибилизатор и способ его получения |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4693885A (en) | 1984-07-18 | 1987-09-15 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| US4675338A (en) * | 1984-07-18 | 1987-06-23 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| US4656186A (en) | 1985-04-30 | 1987-04-07 | Nippon Petrochemicals Co., Ltd. | Tetrapyrrole therapeutic agents |
| US4977177A (en) * | 1985-04-30 | 1990-12-11 | Nippon Petrochemicals Company, Ltd. | Tetrapyrrole polyaminomonocarboxylic acid 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 |
| EP2057169A2 (en) | 2006-06-30 | 2009-05-13 | Light Sciences Oncology, Inc. | Compositions and methods of making a chlorin e6 derivative as a photoactive agent |
-
2007
- 2007-06-29 EP EP07810026A patent/EP2057169A2/en not_active Ceased
- 2007-06-29 KR KR1020097002051A patent/KR101456839B1/ko not_active Expired - Fee Related
- 2007-06-29 JP JP2009518280A patent/JP5323693B2/ja not_active Expired - Fee Related
- 2007-06-29 WO PCT/US2007/015087 patent/WO2008005308A2/en not_active Ceased
- 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 SG SG2011046810A patent/SG172733A1/en unknown
- 2007-06-29 RU RU2009102973/04A patent/RU2009102973A/ru unknown
-
2010
- 2010-11-01 US US12/917,353 patent/US8063203B2/en active Active
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2012
- 2012-05-16 US US13/473,395 patent/US8822677B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US8063203B2 (en) | 2011-11-22 |
| AU2007269784A1 (en) | 2008-01-10 |
| US20110105745A1 (en) | 2011-05-05 |
| SG172733A1 (en) | 2011-07-28 |
| RU2009102973A (ru) | 2010-08-10 |
| US8198312B2 (en) | 2012-06-12 |
| CA2655723C (en) | 2014-11-18 |
| WO2008005308A2 (en) | 2008-01-10 |
| US8822677B2 (en) | 2014-09-02 |
| JP2009542672A (ja) | 2009-12-03 |
| US20080021210A1 (en) | 2008-01-24 |
| WO2008005308A3 (en) | 2008-03-06 |
| CA2655723A1 (en) | 2008-01-10 |
| KR101456839B1 (ko) | 2014-11-03 |
| EP2057169A2 (en) | 2009-05-13 |
| KR20090033463A (ko) | 2009-04-03 |
| AU2007269784B2 (en) | 2012-07-05 |
| CN101490057A (zh) | 2009-07-22 |
| US20130281689A1 (en) | 2013-10-24 |
| CN101490057B (zh) | 2013-02-27 |
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