NZ590054A - Compositions and uses of fingolimod (2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol) - Google Patents
Compositions and uses of fingolimod (2-amino-2-[2-(4-octylphenyl)ethyl]propane-1,3-diol)Info
- Publication number
- NZ590054A NZ590054A NZ590054A NZ59005405A NZ590054A NZ 590054 A NZ590054 A NZ 590054A NZ 590054 A NZ590054 A NZ 590054A NZ 59005405 A NZ59005405 A NZ 59005405A NZ 590054 A NZ590054 A NZ 590054A
- Authority
- NZ
- New Zealand
- Prior art keywords
- fty720
- day
- alkyl
- agonist
- substituted
- Prior art date
Links
- KKGQTZUTZRNORY-UHFFFAOYSA-N fingolimod Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)CO)C=C1 KKGQTZUTZRNORY-UHFFFAOYSA-N 0.000 title claims abstract description 55
- 229960000556 fingolimod Drugs 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 30
- 150000003839 salts Chemical group 0.000 claims abstract description 24
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 3
- 208000005777 Lupus Nephritis Diseases 0.000 claims abstract description 3
- 201000004681 Psoriasis Diseases 0.000 claims abstract description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims abstract description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 102000011011 Sphingosine 1-phosphate receptors Human genes 0.000 description 88
- 108050001083 Sphingosine 1-phosphate receptors Proteins 0.000 description 85
- 229940044601 receptor agonist Drugs 0.000 description 68
- 239000000556 agonist Substances 0.000 description 62
- 229940075993 receptor modulator Drugs 0.000 description 62
- 229910052736 halogen Inorganic materials 0.000 description 49
- 238000011282 treatment Methods 0.000 description 34
- 125000005843 halogen group Chemical group 0.000 description 33
- -1 2-substituted 2-amino- propane-1,3-diol Chemical class 0.000 description 28
- 125000000217 alkyl group Chemical group 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 27
- 229940079593 drug Drugs 0.000 description 26
- 150000002367 halogens Chemical class 0.000 description 24
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 125000002252 acyl group Chemical group 0.000 description 16
- 239000000018 receptor agonist Substances 0.000 description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- 230000036765 blood level Effects 0.000 description 11
- 125000001424 substituent group Chemical group 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000000623 heterocyclic group Chemical group 0.000 description 8
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 210000004698 lymphocyte Anatomy 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 238000012423 maintenance Methods 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 238000009825 accumulation Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 230000002035 prolonged effect Effects 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- 241000282693 Cercopithecidae Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 101100236683 Homo sapiens MBTPS1 gene Proteins 0.000 description 3
- 206010052779 Transplant rejections Diseases 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 210000002216 heart Anatomy 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 238000009115 maintenance therapy Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
- 206010062016 Immunosuppression Diseases 0.000 description 2
- 102000018697 Membrane Proteins Human genes 0.000 description 2
- 108010052285 Membrane Proteins Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000001165 lymph node Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002757 morpholinyl group Chemical group 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 210000001986 peyer's patch Anatomy 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 125000003386 piperidinyl group Chemical group 0.000 description 2
- 239000000902 placebo Substances 0.000 description 2
- 229940068196 placebo Drugs 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000004953 trihalomethyl group Chemical group 0.000 description 2
- GWGANHYLDPKJLO-HSZRJFAPSA-N (2r)-2-amino-4-[3-(4-cyclohexyloxybutyl)-1-benzothiophen-6-yl]-2-methylbutan-1-ol Chemical compound C=1SC2=CC(CC[C@@](N)(CO)C)=CC=C2C=1CCCCOC1CCCCC1 GWGANHYLDPKJLO-HSZRJFAPSA-N 0.000 description 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- FLBPTSOAFRMSPF-UHFFFAOYSA-N 1-[4-[3-amino-4-hydroxy-3-(hydroxymethyl)butyl]phenyl]-5-phenylpentan-1-one Chemical compound C1=CC(CCC(CO)(CO)N)=CC=C1C(=O)CCCCC1=CC=CC=C1 FLBPTSOAFRMSPF-UHFFFAOYSA-N 0.000 description 1
- KIHYPELVXPAIDH-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(C)=NOCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 KIHYPELVXPAIDH-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- BXIWYZLGTUWLCD-UHFFFAOYSA-N 2-amino-2-tetradecylpropane-1,3-diol Chemical compound CCCCCCCCCCCCCCC(N)(CO)CO BXIWYZLGTUWLCD-UHFFFAOYSA-N 0.000 description 1
- ITJCKQTXCLGXHE-UHFFFAOYSA-N 2-amino-4-(4-heptoxyphenyl)-2-methylbutan-1-ol Chemical compound CCCCCCCOC1=CC=C(CCC(C)(N)CO)C=C1 ITJCKQTXCLGXHE-UHFFFAOYSA-N 0.000 description 1
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical class CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UKNPZNCFUIYBMA-UHFFFAOYSA-N 5-amino-5-[2-chloro-4-(2-phenylmethoxyphenyl)sulfanylphenyl]pentane-1,3-diol Chemical compound NC(CC(CCO)O)C1=C(C=C(C=C1)SC1=C(C=CC=C1)OCC1=CC=CC=C1)Cl UKNPZNCFUIYBMA-UHFFFAOYSA-N 0.000 description 1
- NESAWTWENPISNE-UHFFFAOYSA-N 5-amino-5-[2-chloro-4-(3-phenylmethoxyphenoxy)phenyl]hexane-1,3-diol Chemical compound C1=C(Cl)C(C(N)(CC(O)CCO)C)=CC=C1OC1=CC=CC(OCC=2C=CC=CC=2)=C1 NESAWTWENPISNE-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 1
- 101150052147 ALLC gene Proteins 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
- 210000001266 CD8-positive T-lymphocyte Anatomy 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
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- HKVAMNSJSFKALM-GKUWKFKPSA-N Everolimus Chemical compound C1C[C@@H](OCCO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 HKVAMNSJSFKALM-GKUWKFKPSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- LZAPHMLITWOKCL-UHFFFAOYSA-N NC(CC(CCO)O)(C)C1=C(C=C(C=C1)SC1=C(C=CC=C1)OCC1=CC=CC=C1)Cl Chemical compound NC(CC(CCO)O)(C)C1=C(C=C(C=C1)SC1=C(C=CC=C1)OCC1=CC=CC=C1)Cl LZAPHMLITWOKCL-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- URPMOIWBYMBOHA-MRXNPFEDSA-N [(2r)-2-amino-2-methyl-4-(4-pentoxyphenyl)butyl] dihydrogen phosphate Chemical group CCCCCOC1=CC=C(CC[C@@](C)(N)COP(O)(O)=O)C=C1 URPMOIWBYMBOHA-MRXNPFEDSA-N 0.000 description 1
- 238000011292 agonist therapy Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- 238000004458 analytical method Methods 0.000 description 1
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- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- LRFKWQGGENFBFO-UHFFFAOYSA-N fingolimod phosphate Chemical compound CCCCCCCCC1=CC=C(CCC(N)(CO)COP(O)(O)=O)C=C1 LRFKWQGGENFBFO-UHFFFAOYSA-N 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
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Landscapes
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| JP2008509931A (ja) | 2004-08-13 | 2008-04-03 | プレーシス ファーマスーティカルズ インコーポレイテッド | スフィンゴシン−１−ホスフェート（ｓ１ｐ）レセプター活性を調節するための方法および組成物 |
| KR20130041385A (ko) * | 2004-11-29 | 2013-04-24 | 노파르티스 아게 | Ｓ１ｐ 수용체 효능제의 투여 용법 |
| CA2620554C (en) * | 2005-09-09 | 2013-12-17 | Novartis Ag | Treatment of autoimmune diseases |
| GB0612721D0 (en) * | 2006-06-27 | 2006-08-09 | Novartis Ag | Organic compounds |
| KR101526835B1 (ko) | 2007-05-04 | 2015-06-05 | 노파르티스 아게 | Ｓ1ｐ 수용체 조절제의 용도 |
| KR101718639B1 (ko) | 2008-03-17 | 2017-03-21 | 액테리온 파마슈티칼 리미티드 | 선별적 ｓ1ｐ₁ 수용체 작동약에 대한 투약 섭생 |
| RU2505288C2 (ru) * | 2008-05-20 | 2014-01-27 | Киорин Фармасьютикал Ко., Лтд. | Средства поддержания индуцированной ремиссии |
| US9149459B2 (en) * | 2008-07-23 | 2015-10-06 | Novartis Ag | Sphingosine 1 phosphate receptor modulators and their use to treat muscle inflammation |
| RU2523281C2 (ru) * | 2008-08-18 | 2014-07-20 | Новартис Аг | Соединения для лечения периферических невропатий |
| CN103204794A (zh) * | 2008-12-18 | 2013-07-17 | 诺瓦提斯公司 | 新的盐 |
| RU2011129230A (ru) * | 2008-12-18 | 2013-01-27 | Новартис Аг | Новая полиморфная форма 1-[4-[1-(4-циклогексил-3-трифторметилбензилоксиимино)этил]-2-этилбензил]азетидин-3-карбоновой кислоты |
| KR20170062554A (ko) * | 2008-12-18 | 2017-06-07 | 노파르티스 아게 | 1-［4-［1-(4-시클로헥실-3-트리플루오로메틸-벤질옥시이미노)-에틸］-2-에틸-벤질］-아제티딘-3-카르복실산의 헤미푸마레이트 염 |
| JP5657565B2 (ja) * | 2008-12-22 | 2015-01-21 | ノバルティス アーゲー | Ｓ１ｐ受容体アゴニストの投与レジメン |
| HRP20151190T1 (hr) * | 2008-12-22 | 2016-01-01 | Novartis Ag | Režim doziranja za fingolimod u lijeäśenju multiple skleroze |
| AU2015275246B2 (en) * | 2008-12-22 | 2018-02-01 | Novartis Ag | Dosage regimen for a S1P receptor agonist |
| US20120264719A1 (en) * | 2009-09-29 | 2012-10-18 | Craig Boulton | Dosage regimen of an s1p receptor modulator |
| US20110124605A1 (en) * | 2009-11-20 | 2011-05-26 | Shreeram Aradhye | Use of an S1P Receptor Agonist |
| US8791100B2 (en) | 2010-02-02 | 2014-07-29 | Novartis Ag | Aryl benzylamine compounds |
| EP2566473B1 (en) * | 2010-05-06 | 2016-01-06 | Novartis AG | Dosage regimen of diaryl sulfide derivatives |
| BR112013017302B1 (pt) | 2011-01-07 | 2021-12-07 | Novartis Ag | Composição farmacêutica em fase sólida |
| MX2014004813A (es) * | 2011-10-21 | 2014-05-20 | Novartis Ag | Regimen de dosificacion para un modulador o agonista del receptor s1p. |
| SI2885266T1 (sl) | 2012-08-17 | 2020-10-30 | Actelion Pharmaceuticals Ltd | Postopek za pripravo (2Z,5Z)-5-(3-kloro-4-((R)-2,3-dihidroksipropoksi) benziliden)-2-(propilimino)-3-(O-tolil)tiazolidin-4-on in v omenjenem postopku uporabljena vmesna spojina |
| CN102887829B (zh) * | 2012-09-05 | 2014-07-02 | 中国科学院上海药物研究所 | 芬戈莫德粘酸盐及其晶体的制备方法和用途 |
| WO2015053878A1 (en) | 2013-10-11 | 2015-04-16 | Teikoku Pharma Usa, Inc. | Topical sphingosine-1-phosphate receptor agonist formulations and methods of using the same |
| US10675254B2 (en) | 2013-10-11 | 2020-06-09 | Teikoku Seiyaku Co., Ltd. | Sphingosine-1-phosphate receptor agonist iontophoretic devices and methods of using the same |
| WO2016091996A1 (en) | 2014-12-11 | 2016-06-16 | Actelion Pharmaceuticals Ltd | Dosing regimen for a selective s1p1 receptor agonist |
| MA41139A (fr) | 2014-12-11 | 2017-10-17 | Actelion Pharmaceuticals Ltd | Combinaison pharmaceutique comportant un agoniste sélectif du récepteur sip1 |
| US20180042895A1 (en) | 2015-02-26 | 2018-02-15 | Novartis Ag | Treatment of autoimmune disease in a patient receiving additionally a beta-blocker |
| US10250466B2 (en) * | 2016-03-29 | 2019-04-02 | Juniper Networks, Inc. | Application signature generation and distribution |
| US11629124B2 (en) | 2017-03-09 | 2023-04-18 | Novartis Ag | Solid forms comprising an oxime ether compound, compositions and methods of use thereof |
| PH12022551043A1 (en) | 2019-10-31 | 2023-05-03 | Idorsia Pharmaceuticals Ltd | Combination of a cxcr7 antagonist with an s1p1 receptor modulator |
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| DE122011100012I1 (de) | 1992-10-21 | 2011-10-20 | Mitsubishi Tanabe Pharma Corp | 2-Amino-1, 3-propandiolverbindung und immunosuppressium. |
| WO1996006068A1 (en) | 1994-08-22 | 1996-02-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzene compound and medicinal use thereof |
| CA2213989C (en) * | 1995-12-28 | 2007-05-29 | Yoshitomi Pharmaceutical Industries Ltd. | External preparation for topical administration |
| US6476004B1 (en) * | 1996-07-18 | 2002-11-05 | Mitsubishi Pharma Corporation | Pharmaceutical composition |
| KR20000075745A (ko) * | 1997-02-27 | 2000-12-26 | 가마후라 아키오 | 의약 조성물 |
| IL155065A (en) | 1997-04-04 | 2004-01-04 | Mitsubishi Pharma Corp | History - 2 Aminopropene - 1, 3 - Diol and Pharmaceutical Preparations Containing Them |
| JPH1180026A (ja) * | 1997-09-02 | 1999-03-23 | Yoshitomi Pharmaceut Ind Ltd | 新規免疫抑制剤、その使用方法およびその同定方法 |
| JPH11116479A (ja) * | 1997-10-10 | 1999-04-27 | Sugen Inc | 脳癌のための組み合わせ化学療法処置 |
| CN1267429C (zh) | 2000-07-13 | 2006-08-02 | 三共株式会社 | 氨基醇衍生物 |
| CA2421893A1 (en) | 2000-08-31 | 2002-03-07 | Merck And Co., Inc. | Phosphate derivatives as immunoregulatory agents |
| EP1377593B1 (en) | 2001-03-26 | 2005-12-28 | Novartis AG | 2-amino-propanol derivatives |
| WO2002080902A1 (en) * | 2001-04-02 | 2002-10-17 | Astrazeneca Ab | Solid pharmaceutical composition comprising 4 -cyano-trifluoro-3-(4-fluorophenylsulphonyl)-2-hydroxy-2-methylpropiono- m toluidide and pvp |
| ES2364816T3 (es) * | 2001-04-02 | 2011-09-14 | Genentech, Inc. | Terapia de combinación. |
| JP2002316985A (ja) | 2001-04-20 | 2002-10-31 | Sankyo Co Ltd | ベンゾチオフェン誘導体 |
| IL158384A0 (en) * | 2001-06-08 | 2004-05-12 | Novartis Ag | Treatment or prophylaxis of insulin producing cell graft rejection |
| US6963012B2 (en) | 2001-09-27 | 2005-11-08 | Kyorin Pharmaceutical Co., Ltd. | Diaryl ether derivative, addition salt thereof, and immunosuppressant |
| CA2461212C (en) * | 2001-09-27 | 2010-08-17 | Kyorin Pharmaceutical Co., Ltd. | Diaryl sulfide derivatives, salts thereof and immunosuppressive agents using the same |
| WO2003062252A1 (en) | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Edg receptor agonists |
| DE60330047D1 (en) | 2002-01-18 | 2009-12-24 | Merck & Co Inc | "n-(benzyl)aminoalkyl carboxylate, phosphinate, phosphonate und tetrazole als edg rezeptoragonisten" |
| WO2003061567A2 (en) | 2002-01-18 | 2003-07-31 | Merck & Co., Inc. | Selective s1p1/edg1 receptor agonists |
| TWI335311B (en) * | 2002-09-24 | 2011-01-01 | Novartis Ag | Organic compounds |
| MY150088A (en) | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| PE20050158A1 (es) | 2003-05-19 | 2005-05-12 | Irm Llc | Compuestos inmunosupresores y composiciones |
| UA74941C2 (en) | 2004-04-26 | 2006-02-15 | Fos Internat S A | A metal-thermal process for producing magnesium and vacuum induction furnace for realizing the same |
| WO2005113330A1 (en) | 2004-05-05 | 2005-12-01 | Adler, Richard, S. | Systems and methods for protecting ship from attack on the surface or under water |
| WO2006041015A1 (ja) * | 2004-10-12 | 2006-04-20 | Kyorin Pharmaceutical Co., Ltd. | アミノアルコール誘導体とその付加塩及び免疫抑制剤 |
| KR20130041385A (ko) * | 2004-11-29 | 2013-04-24 | 노파르티스 아게 | Ｓ１ｐ 수용체 효능제의 투여 용법 |
| GT200600350A (es) * | 2005-08-09 | 2007-03-28 | Formulaciones líquidas |
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- 2005-11-28 MX MX2007006373A patent/MX2007006373A/es active IP Right Grant
- 2005-11-28 KR KR1020147018084A patent/KR20140095109A/ko not_active Withdrawn
- 2005-11-28 JP JP2007543584A patent/JP2008521827A/ja not_active Withdrawn
- 2005-11-28 EP EP10179083A patent/EP2384749A1/en not_active Withdrawn
- 2005-11-28 NZ NZ554720A patent/NZ554720A/en not_active IP Right Cessation
- 2005-11-28 EP EP05826219.7A patent/EP1819326B1/en not_active Revoked
- 2005-11-28 SG SG2013002662A patent/SG187468A1/en unknown
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2007
- 2007-04-24 ZA ZA200703328A patent/ZA200703328B/xx unknown
- 2007-05-10 NO NO20072401A patent/NO20072401L/no not_active Application Discontinuation
- 2007-05-10 IL IL183134A patent/IL183134A0/en unknown
- 2007-05-22 MA MA29926A patent/MA29034B1/fr unknown
- 2007-05-28 TN TNP2007000209A patent/TNSN07209A1/fr unknown
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2011
- 2011-11-22 US US13/302,881 patent/US20120071446A1/en not_active Abandoned
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2012
- 2012-02-27 JP JP2012040574A patent/JP2012107059A/ja not_active Withdrawn
- 2012-10-02 RU RU2012141951/15A patent/RU2012141951A/ru unknown
- 2012-11-06 NO NO20121305A patent/NO20121305L/no not_active Application Discontinuation
- 2012-12-06 IL IL223502A patent/IL223502A0/en unknown
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2013
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2014
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- 2014-12-26 JP JP2014266267A patent/JP2015061883A/ja active Pending
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