CA2368463A1 - Phosphate containing macrocyclic immunomodulators - Google Patents
Phosphate containing macrocyclic immunomodulators Download PDFInfo
- Publication number
- CA2368463A1 CA2368463A1 CA002368463A CA2368463A CA2368463A1 CA 2368463 A1 CA2368463 A1 CA 2368463A1 CA 002368463 A CA002368463 A CA 002368463A CA 2368463 A CA2368463 A CA 2368463A CA 2368463 A1 CA2368463 A1 CA 2368463A1
- Authority
- CA
- Canada
- Prior art keywords
- minor
- group
- ethyl
- dioxa
- tetraoxo
- 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
- 229910019142 PO4 Inorganic materials 0.000 title claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 title claims description 15
- 239000010452 phosphate Substances 0.000 title claims description 15
- 239000002955 immunomodulating agent Substances 0.000 title abstract description 4
- 229940121354 immunomodulator Drugs 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 121
- 238000000034 method Methods 0.000 claims abstract description 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 109
- -1 thiomorpholine sulfone Chemical class 0.000 claims description 77
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 41
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 22
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 16
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 201000004624 Dermatitis Diseases 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000000651 prodrug Substances 0.000 claims description 10
- 229940002612 prodrug Drugs 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 210000000056 organ Anatomy 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 229930192474 thiophene Natural products 0.000 claims description 7
- 210000001519 tissue Anatomy 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000002519 immonomodulatory effect Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 210000004072 lung Anatomy 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 208000010668 atopic eczema Diseases 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 210000003734 kidney Anatomy 0.000 claims description 4
- 210000004185 liver Anatomy 0.000 claims description 4
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
- XBSSITSLAOYXQW-UHFFFAOYSA-N (4-fluorophenyl)methyl methyl hydrogen phosphate Chemical compound COP(O)(=O)OCC1=CC=C(F)C=C1 XBSSITSLAOYXQW-UHFFFAOYSA-N 0.000 claims description 3
- 210000004087 cornea Anatomy 0.000 claims description 3
- 210000002216 heart Anatomy 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- HXJZHJLLMIGFCM-UHFFFAOYSA-N hydroxy-imino-di(propan-2-yloxy)-$l^{5}-phosphane Chemical compound CC(C)OP(N)(=O)OC(C)C HXJZHJLLMIGFCM-UHFFFAOYSA-N 0.000 claims description 3
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 3
- JRPSUKHOMUIFMO-UHFFFAOYSA-N methoxy-N,N-di(propan-2-yl)phosphonamidic acid Chemical compound COP(O)(=O)N(C(C)C)C(C)C JRPSUKHOMUIFMO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 3
- CHMPKAGUWBJYOA-UHFFFAOYSA-N (3-iodophenyl) methyl hydrogen phosphate Chemical compound COP(O)(=O)OC1=CC=CC(I)=C1 CHMPKAGUWBJYOA-UHFFFAOYSA-N 0.000 claims description 2
- RFCVVMNZNHZOEU-UHFFFAOYSA-N (4-formylphenyl) methyl hydrogen phosphate Chemical compound COP(O)(=O)OC1=CC=C(C=O)C=C1 RFCVVMNZNHZOEU-UHFFFAOYSA-N 0.000 claims description 2
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 208000028185 Angioedema Diseases 0.000 claims description 2
- 206010014950 Eosinophilia Diseases 0.000 claims description 2
- 206010014989 Epidermolysis bullosa Diseases 0.000 claims description 2
- 206010015150 Erythema Diseases 0.000 claims description 2
- 206010034277 Pemphigoid Diseases 0.000 claims description 2
- 241000721454 Pemphigus Species 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 208000024780 Urticaria Diseases 0.000 claims description 2
- 206010047112 Vasculitides Diseases 0.000 claims description 2
- 206010047115 Vasculitis Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- 208000004631 alopecia areata Diseases 0.000 claims description 2
- 208000000594 bullous pemphigoid Diseases 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 2
- 210000001198 duodenum Anatomy 0.000 claims description 2
- 231100000321 erythema Toxicity 0.000 claims description 2
- KCSLERVBHQGNFH-UHFFFAOYSA-N furan-3-ylmethyl methyl hydrogen phosphate Chemical compound COP(O)(=O)OCC=1C=COC=1 KCSLERVBHQGNFH-UHFFFAOYSA-N 0.000 claims description 2
- 210000000987 immune system Anatomy 0.000 claims description 2
- 201000011486 lichen planus Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- IGKBJEYTLFFEGN-UHFFFAOYSA-N methyl (4-nitrophenyl)methyl hydrogen phosphate Chemical compound COP(O)(=O)OCC1=CC=C([N+]([O-])=O)C=C1 IGKBJEYTLFFEGN-UHFFFAOYSA-N 0.000 claims description 2
- FHYGQENFUMEVHD-UHFFFAOYSA-N methyl 2-morpholin-4-ylethyl hydrogen phosphate Chemical compound COP(=O)(O)OCCN1CCOCC1 FHYGQENFUMEVHD-UHFFFAOYSA-N 0.000 claims description 2
- MEPUMKJCWQABJY-UHFFFAOYSA-N methyl 2-pyrrolidin-1-ylethyl hydrogen phosphate Chemical compound COP(=O)(O)OCCN1CCCC1 MEPUMKJCWQABJY-UHFFFAOYSA-N 0.000 claims description 2
- JBOHDBCPSKADRQ-UHFFFAOYSA-N methyl pyridin-2-ylmethyl hydrogen phosphate Chemical compound COP(=O)(O)OCC1=CC=CC=N1 JBOHDBCPSKADRQ-UHFFFAOYSA-N 0.000 claims description 2
- UDAUCQCVCCVVLI-UHFFFAOYSA-N methyl pyridin-3-ylmethyl hydrogen phosphate Chemical compound COP(O)(=O)OCC1=CC=CN=C1 UDAUCQCVCCVVLI-UHFFFAOYSA-N 0.000 claims description 2
- MMWIAKJVUCIOMO-UHFFFAOYSA-N methyl pyridin-4-ylmethyl hydrogen phosphate Chemical compound COP(=O)(O)OCC1=CC=NC=C1 MMWIAKJVUCIOMO-UHFFFAOYSA-N 0.000 claims description 2
- GHTGFISXVVLKQT-UHFFFAOYSA-N methyl thiophen-3-ylmethyl hydrogen phosphate Chemical compound COP(=O)(O)OCC1=CSC=C1 GHTGFISXVVLKQT-UHFFFAOYSA-N 0.000 claims description 2
- 210000003205 muscle Anatomy 0.000 claims description 2
- 210000000496 pancreas Anatomy 0.000 claims description 2
- HXAWNCLRGFULKN-UHFFFAOYSA-N (4-fluorophenyl) methyl hydrogen phosphate Chemical compound COP(O)(=O)OC1=CC=C(F)C=C1 HXAWNCLRGFULKN-UHFFFAOYSA-N 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 32
- 239000003018 immunosuppressive agent Substances 0.000 abstract description 11
- 229960003444 immunosuppressant agent Drugs 0.000 abstract description 10
- 239000003120 macrolide antibiotic agent Substances 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 216
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 82
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 40
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 29
- 125000004076 pyridyl group Chemical group 0.000 description 29
- 239000000243 solution Substances 0.000 description 29
- JUJWROOIHBZHMG-QYKNYGDISA-N 2-deuteriopyridine Chemical compound [2H]C1=CC=CC=N1 JUJWROOIHBZHMG-QYKNYGDISA-N 0.000 description 28
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- ZDQSOHOQTUFQEM-NURRSENYSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-NURRSENYSA-N 0.000 description 19
- 235000021317 phosphate Nutrition 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229940079593 drug Drugs 0.000 description 15
- 239000003814 drug Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 201000010099 disease Diseases 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- 229910001868 water Inorganic materials 0.000 description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
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- 210000004369 blood Anatomy 0.000 description 9
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 8
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 8
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 7
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 238000002054 transplantation Methods 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241000187747 Streptomyces Species 0.000 description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
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- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- ZCWKIFAQRXNZCH-UHFFFAOYSA-M tetramethylazanium;perchlorate Chemical compound C[N+](C)(C)C.[O-]Cl(=O)(=O)=O ZCWKIFAQRXNZCH-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036575 thermal burns Effects 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical group C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- RLTPJVKHGBFGQA-UHFFFAOYSA-N thiadiazolidine Chemical group C1CSNN1 RLTPJVKHGBFGQA-UHFFFAOYSA-N 0.000 description 1
- GVIJJXMXTUZIOD-UHFFFAOYSA-N thianthrene Chemical compound C1=CC=C2SC3=CC=CC=C3SC2=C1 GVIJJXMXTUZIOD-UHFFFAOYSA-N 0.000 description 1
- CBDKQYKMCICBOF-UHFFFAOYSA-N thiazoline Chemical group C1CN=CS1 CBDKQYKMCICBOF-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical group S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 201000005539 vernal conjunctivitis Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 201000001862 viral hepatitis Diseases 0.000 description 1
- 238000003260 vortexing Methods 0.000 description 1
- 210000003905 vulva Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Transplantation (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28313199A | 1999-03-31 | 1999-03-31 | |
US09/283,131 | 1999-03-31 | ||
PCT/US2000/007639 WO2000058318A1 (en) | 1999-03-31 | 2000-03-23 | Phosphate containing macrocyclic immunomodulators |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2368463A1 true CA2368463A1 (en) | 2000-10-05 |
Family
ID=23084671
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002368463A Abandoned CA2368463A1 (en) | 1999-03-31 | 2000-03-23 | Phosphate containing macrocyclic immunomodulators |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1165575A1 (de) |
JP (1) | JP2002540211A (de) |
CA (1) | CA2368463A1 (de) |
MX (1) | MXPA01009935A (de) |
WO (1) | WO2000058318A1 (de) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110104186A1 (en) | 2004-06-24 | 2011-05-05 | Nicholas Valiante | Small molecule immunopotentiators and assays for their detection |
CA3043575A1 (en) * | 2016-11-10 | 2018-05-17 | Novartis Ag | Bmp potentiators |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4894366A (en) * | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
EP0323865A1 (de) * | 1988-01-07 | 1989-07-12 | Merck & Co. Inc. | Immunopressantes Mittel |
WO1993004679A1 (en) * | 1991-09-05 | 1993-03-18 | Abbott Laboratories | Macrocyclic immunomodulators |
US5457111A (en) * | 1991-09-05 | 1995-10-10 | Abbott Laboratories | Macrocyclic immunomodulators |
US5457194A (en) * | 1993-03-17 | 1995-10-10 | Abbott Laboratories | Substituted aliphatic amine-containing macrocyclic immunomodulators |
-
2000
- 2000-03-23 EP EP00918274A patent/EP1165575A1/de not_active Withdrawn
- 2000-03-23 JP JP2000608018A patent/JP2002540211A/ja not_active Withdrawn
- 2000-03-23 MX MXPA01009935A patent/MXPA01009935A/es not_active Application Discontinuation
- 2000-03-23 CA CA002368463A patent/CA2368463A1/en not_active Abandoned
- 2000-03-23 WO PCT/US2000/007639 patent/WO2000058318A1/en not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
EP1165575A1 (de) | 2002-01-02 |
MXPA01009935A (es) | 2002-05-06 |
WO2000058318A1 (en) | 2000-10-05 |
JP2002540211A (ja) | 2002-11-26 |
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Legal Events
Date | Code | Title | Description |
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FZDE | Dead |