CA2533128A1 - Bioactive compositions comprising triazines - Google Patents
Bioactive compositions comprising triazines Download PDFInfo
- Publication number
- CA2533128A1 CA2533128A1 CA002533128A CA2533128A CA2533128A1 CA 2533128 A1 CA2533128 A1 CA 2533128A1 CA 002533128 A CA002533128 A CA 002533128A CA 2533128 A CA2533128 A CA 2533128A CA 2533128 A1 CA2533128 A1 CA 2533128A1
- Authority
- CA
- Canada
- Prior art keywords
- bioactive
- compound
- group
- triazine
- composition according
- 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.)
- Abandoned
Links
- 230000000975 bioactive effect Effects 0.000 title claims abstract description 152
- 239000000203 mixture Substances 0.000 title claims abstract description 97
- 150000003918 triazines Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- -1 triazine compound Chemical class 0.000 claims abstract description 96
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 50
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 230000007935 neutral effect Effects 0.000 claims abstract description 16
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims description 34
- 229940079593 drug Drugs 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002552 dosage form Substances 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 230000001965 increasing effect Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 238000012377 drug delivery Methods 0.000 claims description 5
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000007927 intramuscular injection Substances 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims description 3
- 238000010255 intramuscular injection Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 238000010253 intravenous injection Methods 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 18
- 239000012071 phase Substances 0.000 description 14
- 229940062527 alendronate Drugs 0.000 description 9
- 229960002751 imiquimod Drugs 0.000 description 9
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- DOUYETYNHWVLEO-UHFFFAOYSA-N imiquimod Chemical compound C1=CC=CC2=C3N(CC(C)C)C=NC3=C(N)N=C21 DOUYETYNHWVLEO-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229960004194 lidocaine Drugs 0.000 description 6
- NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 5
- 150000004820 halides Chemical group 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000011550 stock solution Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- ZQFZZABRAAUHTA-UHFFFAOYSA-N 4-[[4-(4-carboxyanilino)-6-[4-(dimethylamino)pyridin-1-ium-1-yl]-1,3,5-triazin-2-yl]amino]benzoic acid;chloride Chemical compound [Cl-].C1=CC(N(C)C)=CC=[N+]1C1=NC(NC=2C=CC(=CC=2)C(O)=O)=NC(NC=2C=CC(=CC=2)C(O)=O)=N1 ZQFZZABRAAUHTA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 2
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- 150000003841 chloride salts Chemical class 0.000 description 2
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
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Classifications
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- C07—ORGANIC CHEMISTRY
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- 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
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- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
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- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US60/491,638 | 2003-07-31 | ||
| PCT/US2004/024515 WO2005011629A1 (en) | 2003-07-31 | 2004-07-29 | Bioactive compositions comprising triazines |
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| CA002534042A Abandoned CA2534042A1 (en) | 2003-07-31 | 2004-07-29 | Compositions for encapsulation and controlled release |
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| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| CA2536136C (en) * | 2003-08-27 | 2012-10-30 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| US8871782B2 (en) | 2003-10-03 | 2014-10-28 | 3M Innovative Properties Company | Alkoxy substituted imidazoquinolines |
| EP1696912B1 (en) | 2003-10-03 | 2016-05-11 | 3M Innovative Properties Company | Pyrazolopyridines and analogs thereof |
| MY161812A (en) | 2003-11-25 | 2017-05-15 | 3M Innovative Properties Co | Substituted imidazo ring systems and methods |
| US8541438B2 (en) * | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
| US7687115B2 (en) | 2004-11-24 | 2010-03-30 | 3M Innovative Properties Company | Method for making nanostructured surfaces |
| US7582330B2 (en) | 2004-11-24 | 2009-09-01 | 3M Innovative Properties Counsel | Method for making metallic nanostructures |
| US7247723B2 (en) | 2004-11-24 | 2007-07-24 | 3M Innovative Properties Company | Metallic chromonic compounds |
| CA2592904C (en) | 2004-12-30 | 2015-04-07 | 3M Innovative Properties Company | Chiral fused [1,2]imidazo[4,5-c] ring compounds |
| JP5313502B2 (ja) | 2004-12-30 | 2013-10-09 | スリーエム イノベイティブ プロパティズ カンパニー | 置換キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物 |
| CA2602083A1 (en) | 2005-02-09 | 2006-08-09 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazolo(4,5-c) ring compounds and methods |
| WO2006086449A2 (en) | 2005-02-09 | 2006-08-17 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| JP2008532933A (ja) * | 2005-02-11 | 2008-08-21 | コーリー ファーマシューティカル グループ，インコーポレイテッド | 置換イミダゾキノリン類および置換イミダゾナフチリジン類 |
| WO2006098852A2 (en) * | 2005-02-23 | 2006-09-21 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazoquinolines |
| US8846710B2 (en) * | 2005-02-23 | 2014-09-30 | 3M Innovative Properties Company | Method of preferentially inducing the biosynthesis of interferon |
| AU2006216799A1 (en) | 2005-02-23 | 2006-08-31 | Coley Pharmaceutical Group, Inc. | Hydroxyalkyl substituted imidazonaphthyridines |
| JP2008531567A (ja) * | 2005-02-23 | 2008-08-14 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ヒドロキシアルキル置換イミダゾキノリン化合物および方法 |
| EP1896007B1 (en) | 2005-05-04 | 2014-03-19 | Medigene AG | Method of administering a cationic liposomal preparation comprising paclitexel |
| CA2621831A1 (en) * | 2005-09-09 | 2007-03-15 | Coley Pharmaceutical Group, Inc. | Amide and carbamate derivatives of n-{2-[4-amino-2- (ethoxymethyl)-1h-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide and methods |
| ZA200803029B (en) | 2005-09-09 | 2009-02-25 | Coley Pharm Group Inc | Amide and carbamate derivatives of alkyl substituted /V-[4-(4-amino-1H-imidazo[4,5-c] quinolin-1-yl)butyl] methane-sulfonamides and methods |
| US7629027B2 (en) | 2005-10-14 | 2009-12-08 | 3M Innovative Properties Company | Method for making chromonic nanoparticles |
| US7718716B2 (en) | 2005-10-14 | 2010-05-18 | 3M Innovative Properties Company | Chromonic nanoparticles containing bioactive compounds |
| CN101309687A (zh) | 2005-11-04 | 2008-11-19 | 科勒制药集团公司 | 经羟基和烷氧基取代的1h-咪唑并喹啉及其方法 |
| US7807661B2 (en) | 2005-12-08 | 2010-10-05 | 3M Innovative Properties Company | Silver ion releasing articles and methods of manufacture |
| US7601769B2 (en) * | 2005-12-19 | 2009-10-13 | 3M Innovative Peroperties Company | Multilayered chromonic structures |
| US8092710B2 (en) * | 2005-12-19 | 2012-01-10 | 3M Innovative Properties Company | Hierarchical chromonic structures |
| GB0526291D0 (en) | 2005-12-23 | 2006-02-01 | Prosidion Ltd | Therapeutic method |
| US7824732B2 (en) | 2005-12-28 | 2010-11-02 | 3M Innovative Properties Company | Encapsulated chromonic particles |
| US8951528B2 (en) | 2006-02-22 | 2015-02-10 | 3M Innovative Properties Company | Immune response modifier conjugates |
| WO2007106854A2 (en) * | 2006-03-15 | 2007-09-20 | Coley Pharmaceutical Group, Inc. | Hydroxy and alkoxy substituted 1h-imidazonaphthyridines and methods |
| WO2007107305A2 (en) | 2006-03-22 | 2007-09-27 | Medigene Ag | Treatment of triple receptor negative breast cancer |
| US20070243258A1 (en) * | 2006-04-13 | 2007-10-18 | 3M Innovative Properties Company | Method and apparatus for forming crosslinked chromonic nanoparticles |
| US20070275185A1 (en) * | 2006-05-23 | 2007-11-29 | 3M Innovative Properties Company | Method of making ordered nanostructured layers |
| WO2008030511A2 (en) * | 2006-09-06 | 2008-03-13 | Coley Pharmaceuticial Group, Inc. | Substituted 3,4,6,7-tetrahydro-5h, 1,2a,4a,8-tetraazacyclopenta[cd]phenalenes |
| CN101568351B (zh) * | 2006-12-22 | 2012-05-30 | 3M创新有限公司 | 控制释放的组合物和方法 |
| WO2009139939A2 (en) * | 2008-02-22 | 2009-11-19 | The University Of North Carolina At Chapel Hill | Hybrid nanoparticles as anti-cancer therapeutic agents and dual therapeutic/imaging contrast agents |
| MX339903B (es) | 2009-02-13 | 2016-06-15 | Monsanto Technology Llc | Encapsulacion de herbicidas para reducir daños en cultivos. |
| US20120094281A1 (en) * | 2009-05-06 | 2012-04-19 | Raj Rajagopal | Articles with shell structures including a cell extractant and biodetection methods thereof |
| WO2012024284A1 (en) | 2010-08-17 | 2012-02-23 | 3M Innovative Properties Company | Lipidated immune response modifier compound compositions, formulations, and methods |
| BR112013004485B1 (pt) | 2010-08-18 | 2022-02-08 | Monsanto Technology Llc | Método para controle de ervas daninhas em campo de plantas de cultura |
| JP6415979B2 (ja) | 2011-06-03 | 2018-10-31 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドラジノ１ｈ−イミダゾキノリン−４−アミン及びこれから調製された複合体 |
| JP6460789B2 (ja) | 2011-06-03 | 2019-01-30 | スリーエム イノベイティブ プロパティズ カンパニー | ポリエチレングリコールセグメントを有するヘテロ２官能性リンカー及び該リンカーから調製された免疫反応調節複合体 |
| EP3494974B1 (en) | 2011-07-08 | 2023-10-18 | The University of North Carolina at Chapel Hill | Metal bisphosphonate nanoparticles for anti-cancer therapy and imaging and for treating bone disorders |
| JP6590802B2 (ja) | 2013-11-06 | 2019-10-16 | ザ ユニバーシティ オブ シカゴＴｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃｈｉｃａｇｏ | 化学療法用薬剤、核酸及び光増感剤の送達又は共送達のためのナノスケール輸送体 |
| UY40114A (es) | 2014-01-27 | 2023-02-28 | Monsanto Technology Llc | Composiciones herbicidas concentradas acuosas que contienen microcápsulas (acetocloro), fomesafen, un espesante pseudoplástico y un agente rompedor de estructuras (urea) |
| CN110731961A (zh) | 2014-10-14 | 2020-01-31 | 芝加哥大学 | 金属有机框架、药物制剂及其在制备药物中的用途 |
| US10806694B2 (en) | 2014-10-14 | 2020-10-20 | The University Of Chicago | Nanoparticles for photodynamic therapy, X-ray induced photodynamic therapy, radiotherapy, radiodynamic therapy, chemotherapy, immunotherapy, and any combination thereof |
| WO2016178224A1 (en) * | 2015-05-05 | 2016-11-10 | B. G. Negev Technologies And Applications Ltd | Anionic nanoparticles for use in the delivery of anionic small molecule drugs |
| JP7090034B2 (ja) | 2016-05-20 | 2022-06-23 | ザ ユニバーシティ オブ シカゴ | 化学療法、標的療法、光線力学療法、免疫療法及びそれらの任意の組み合わせのためのナノ粒子 |
| WO2018231913A1 (en) | 2017-06-13 | 2018-12-20 | Monsanto Technology Llc | Microencapsulated herbicides |
| JP7364552B2 (ja) | 2017-08-02 | 2023-10-18 | ザ ユニバーシティ オブ シカゴ | Ｘ線誘起光線力学療法、放射線療法、放射線力学療法、化学療法、免疫療法、及びそれらの任意の組み合わせのための、ナノスケール金属有機層及び金属有機ナノプレート |
| US11306083B2 (en) | 2017-12-20 | 2022-04-19 | 3M Innovative Properties Company | Amide substituted imidazo[4,5-C]quinoline compounds with a branched chain linking group for use as an immune response modifier |
| UA129154C2 (uk) | 2019-01-30 | 2025-01-29 | Монсанто Текнолоджі Ллс | Мікрокапсульовані ацетамідні гербіциди |
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| US5939090A (en) * | 1996-12-03 | 1999-08-17 | 3M Innovative Properties Company | Gel formulations for topical drug delivery |
| EP0894797A4 (en) * | 1997-01-09 | 2001-08-16 | Terumo Corp | NEW AMID DERIVATIVES AND INTERMEDIATES ON YOUR SYNTHESIS |
| US6406705B1 (en) * | 1997-03-10 | 2002-06-18 | University Of Iowa Research Foundation | Use of nucleic acids containing unmethylated CpG dinucleotide as an adjuvant |
| US6248364B1 (en) * | 1997-04-07 | 2001-06-19 | 3M Innovative Properties Company | Encapsulation process and encapsulated products |
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| US6339068B1 (en) * | 1997-05-20 | 2002-01-15 | University Of Iowa Research Foundation | Vectors and methods for immunization or therapeutic protocols |
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| US6110929A (en) * | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
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| US6331539B1 (en) * | 1999-06-10 | 2001-12-18 | 3M Innovative Properties Company | Sulfonamide and sulfamide substituted imidazoquinolines |
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| US6574044B1 (en) * | 1999-10-25 | 2003-06-03 | 3M Innovative Properties Company | Polarizer constructions and display devices exhibiting unique color effects |
| US6538714B1 (en) * | 1999-10-25 | 2003-03-25 | 3M Innovative Properties Company | Dual color guest-host polarizers and devices containing guest-host polarizers |
| US6376669B1 (en) * | 1999-11-05 | 2002-04-23 | 3M Innovative Properties Company | Dye labeled imidazoquinoline compounds |
| WO2001035161A1 (en) * | 1999-11-12 | 2001-05-17 | 3M Innovative Properties Company | Liquid crystal alignment structures and optical devices containing same |
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| US20020055517A1 (en) * | 2000-09-15 | 2002-05-09 | 3M Innovative Properties Company | Methods for delaying recurrence of herpes virus symptoms |
| US6488866B1 (en) * | 2000-11-08 | 2002-12-03 | 3M Innovative Properties Company | Liquid crystal materials and alignment structures and optical devices containing same |
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| US6525064B1 (en) * | 2000-12-08 | 2003-02-25 | 3M Innovative Properties Company | Sulfonamido substituted imidazopyridines |
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-
2004
- 2004-07-29 JP JP2006522048A patent/JP2007500712A/ja not_active Withdrawn
- 2004-07-29 JP JP2006522067A patent/JP2007500713A/ja not_active Withdrawn
- 2004-07-29 EP EP04779475A patent/EP1651035A2/en not_active Withdrawn
- 2004-07-29 WO PCT/US2004/024515 patent/WO2005011629A1/en not_active Ceased
- 2004-07-29 EP EP04779530A patent/EP1651185A1/en not_active Withdrawn
- 2004-07-29 RU RU2006102187/15A patent/RU2006102187A/ru unknown
- 2004-07-29 KR KR1020067001969A patent/KR20060054371A/ko not_active Withdrawn
- 2004-07-29 WO PCT/US2004/024429 patent/WO2005012488A2/en not_active Ceased
- 2004-07-29 MX MXPA06001004A patent/MXPA06001004A/es unknown
- 2004-07-29 BR BRPI0413164-9A patent/BRPI0413164A/pt not_active Application Discontinuation
- 2004-07-29 AU AU2004261987A patent/AU2004261987A1/en not_active Abandoned
- 2004-07-29 CA CA002533128A patent/CA2533128A1/en not_active Abandoned
- 2004-07-29 BR BRPI0413143-6A patent/BRPI0413143A/pt not_active Application Discontinuation
- 2004-07-29 US US10/595,051 patent/US20080063714A1/en not_active Abandoned
- 2004-07-29 KR KR1020067001970A patent/KR20060056354A/ko not_active Withdrawn
- 2004-07-29 MX MXPA06001054A patent/MXPA06001054A/es unknown
- 2004-07-29 AU AU2004261243A patent/AU2004261243A1/en not_active Abandoned
- 2004-07-29 CA CA002534042A patent/CA2534042A1/en not_active Abandoned
- 2004-07-29 US US10/595,050 patent/US20080039533A1/en not_active Abandoned
- 2004-07-29 RU RU2006102188/04A patent/RU2006102188A/ru unknown
-
2006
- 2006-01-23 IL IL173301A patent/IL173301A0/en unknown
- 2006-01-23 IL IL173300A patent/IL173300A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0413143A (pt) | 2006-10-03 |
| WO2005011629A1 (en) | 2005-02-10 |
| KR20060054371A (ko) | 2006-05-22 |
| JP2007500713A (ja) | 2007-01-18 |
| JP2007500712A (ja) | 2007-01-18 |
| EP1651185A1 (en) | 2006-05-03 |
| CA2534042A1 (en) | 2005-02-10 |
| BRPI0413164A (pt) | 2006-10-03 |
| MXPA06001004A (es) | 2006-04-27 |
| RU2006102187A (ru) | 2006-08-10 |
| MXPA06001054A (es) | 2006-04-24 |
| WO2005012488A3 (en) | 2005-05-26 |
| EP1651035A2 (en) | 2006-05-03 |
| US20080039533A1 (en) | 2008-02-14 |
| KR20060056354A (ko) | 2006-05-24 |
| US20080063714A1 (en) | 2008-03-13 |
| IL173301A0 (en) | 2006-06-11 |
| IL173300A0 (en) | 2006-06-11 |
| WO2005012488A2 (en) | 2005-02-10 |
| RU2006102188A (ru) | 2006-07-10 |
| AU2004261243A1 (en) | 2005-02-10 |
| AU2004261987A1 (en) | 2005-02-10 |
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| FZDE | Discontinued |