JP2015519368A5 - - Google Patents
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- JP2015519368A5 JP2015519368A5 JP2015515175A JP2015515175A JP2015519368A5 JP 2015519368 A5 JP2015519368 A5 JP 2015519368A5 JP 2015515175 A JP2015515175 A JP 2015515175A JP 2015515175 A JP2015515175 A JP 2015515175A JP 2015519368 A5 JP2015519368 A5 JP 2015519368A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- methylamino
- hydroxy
- sar
- 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.)
- Pending
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- 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 claims 137
- 150000001875 compounds Chemical class 0.000 claims 97
- 229930105110 Cyclosporin A Natural products 0.000 claims 82
- 108010036949 Cyclosporine Proteins 0.000 claims 82
- 229960001265 ciclosporin Drugs 0.000 claims 80
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 69
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 38
- -1 piperazinonyl Chemical group 0.000 claims 34
- 125000000623 heterocyclic group Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 4
- 239000000706 filtrate Substances 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 206010061218 Inflammation Diseases 0.000 claims 3
- 230000004054 inflammatory process Effects 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 3
- 238000005406 washing Methods 0.000 claims 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 208000003556 Dry Eye Syndromes Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 230000004489 tear production Effects 0.000 claims 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 claims 1
- SFFSGPCYJCMDJM-UHFFFAOYSA-N 2-[2-(3-oxo-1,2-benzoselenazol-2-yl)ethyl]-1,2-benzoselenazol-3-one Chemical compound [se]1C2=CC=CC=C2C(=O)N1CCN1C(=O)C(C=CC=C2)=C2[se]1 SFFSGPCYJCMDJM-UHFFFAOYSA-N 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 208000009137 Behcet syndrome Diseases 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010013774 Dry eye Diseases 0.000 claims 1
- 206010015946 Eye irritation Diseases 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 208000005100 Herpetic Keratitis Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010022941 Iridocyclitis Diseases 0.000 claims 1
- 206010073938 Ophthalmic herpes simplex Diseases 0.000 claims 1
- 241000721454 Pemphigus Species 0.000 claims 1
- 201000002154 Pterygium Diseases 0.000 claims 1
- 241001303601 Rosacea Species 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 1
- 206010042033 Stevens-Johnson syndrome Diseases 0.000 claims 1
- 231100000168 Stevens-Johnson syndrome Toxicity 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 108010021119 Trichosanthin Proteins 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- 150000001299 aldehydes Chemical class 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 201000004612 anterior uveitis Diseases 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 206010069664 atopic keratoconjunctivitis Diseases 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
- 125000005513 benzoazaindolyl group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
- 208000010217 blepharitis Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 claims 1
- 210000004087 cornea Anatomy 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 231100000013 eye irritation Toxicity 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000003838 furazanyl group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 claims 1
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 125000005945 imidazopyridyl group Chemical group 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 201000010666 keratoconjunctivitis Diseases 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 150000003951 lactams Chemical class 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000004175 meibomian gland Anatomy 0.000 claims 1
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000004095 oxindolyl group Chemical group N1(C(CC2=CC=CC=C12)=O)* 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims 1
- 125000005936 piperidyl group Chemical group 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 230000037390 scarring Effects 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005505 thiomorpholino group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- YYQGIBVMSBPIEC-UHFFFAOYSA-N CNCC1OCCOC1 Chemical compound CNCC1OCCOC1 YYQGIBVMSBPIEC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261654388P | 2012-06-01 | 2012-06-01 | |
| US61/654,388 | 2012-06-01 | ||
| PCT/US2013/043266 WO2013181339A2 (en) | 2012-06-01 | 2013-05-30 | Cyclosporin a analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015519368A JP2015519368A (ja) | 2015-07-09 |
| JP2015519368A5 true JP2015519368A5 (https=) | 2016-07-28 |
Family
ID=48577956
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015515175A Pending JP2015519368A (ja) | 2012-06-01 | 2013-05-30 | シクロスポリンａ類似体 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9266927B2 (https=) |
| EP (2) | EP3263587A1 (https=) |
| JP (1) | JP2015519368A (https=) |
| CN (1) | CN104487449A (https=) |
| AU (1) | AU2013267435B2 (https=) |
| CA (1) | CA2874548A1 (https=) |
| TW (1) | TW201408702A (https=) |
| WO (1) | WO2013181339A2 (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9890198B2 (en) | 2010-12-03 | 2018-02-13 | S&T Global Inc. | Cyclosporin derivatives and uses thereof |
| BR112015021388A2 (pt) | 2013-03-08 | 2017-07-18 | Allergan Inc | conjugados esteroides de ciclosporina a |
| US9914755B2 (en) | 2015-01-08 | 2018-03-13 | Allergan, Inc. | Cyclosporin derivatives wherein the MeBmt sidechain has been cyclized |
| EP3277704A1 (en) | 2015-03-31 | 2018-02-07 | Allergan, Inc. | Cyclosporins modified on the mebmt sidechain by heterocyclic rings |
| WO2017004304A1 (en) * | 2015-06-30 | 2017-01-05 | Cypralis Limited | Novel macrocycles |
| CN118324867A (zh) * | 2016-05-17 | 2024-07-12 | 美国科技环球有限公司 | 新型环孢菌素衍生物及其用途 |
| WO2019246312A1 (en) | 2018-06-20 | 2019-12-26 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with an immunomodulator |
| WO2020163594A1 (en) | 2019-02-07 | 2020-08-13 | The Regents Of The University Of California | Immunophilin binding agents and uses thereof |
| GB202007106D0 (en) * | 2020-05-14 | 2020-07-01 | Ucl Business Plc | Cyclosporine analogues |
| IL278473A (en) | 2020-11-03 | 2022-06-01 | Yeda Res & Dev | Methods for diagnosing and determining treatment in multiple myeloma |
| CN115028679B (zh) * | 2022-08-11 | 2022-11-15 | 深圳湾实验室 | 一种具有Cyclophilin A降解活性的PROTAC化合物及其制备方法与应用 |
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-
2013
- 2013-05-30 JP JP2015515175A patent/JP2015519368A/ja active Pending
- 2013-05-30 EP EP17184903.7A patent/EP3263587A1/en not_active Withdrawn
- 2013-05-30 CN CN201380038907.0A patent/CN104487449A/zh active Pending
- 2013-05-30 AU AU2013267435A patent/AU2013267435B2/en not_active Ceased
- 2013-05-30 CA CA2874548A patent/CA2874548A1/en not_active Abandoned
- 2013-05-30 EP EP13727787.7A patent/EP2855508B1/en not_active Not-in-force
- 2013-05-30 US US13/905,491 patent/US9266927B2/en active Active
- 2013-05-30 WO PCT/US2013/043266 patent/WO2013181339A2/en not_active Ceased
- 2013-05-31 TW TW102119527A patent/TW201408702A/zh unknown
-
2015
- 2015-08-12 US US14/824,392 patent/US20160039880A1/en not_active Abandoned
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