JP2019515014A5 - - Google Patents
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- JP2019515014A5 JP2019515014A5 JP2018559881A JP2018559881A JP2019515014A5 JP 2019515014 A5 JP2019515014 A5 JP 2019515014A5 JP 2018559881 A JP2018559881 A JP 2018559881A JP 2018559881 A JP2018559881 A JP 2018559881A JP 2019515014 A5 JP2019515014 A5 JP 2019515014A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- compound
- nhc
- halo
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 468
- 150000001875 compounds Chemical class 0.000 claims description 147
- 229910052739 hydrogen Inorganic materials 0.000 claims description 96
- 125000005843 halogen group Chemical group 0.000 claims description 82
- 239000001257 hydrogen Substances 0.000 claims description 77
- 229910052736 halogen Inorganic materials 0.000 claims description 56
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 50
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 46
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000468 ketone group Chemical group 0.000 claims description 23
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 22
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000012453 solvate Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229930194542 Keto Natural products 0.000 claims description 8
- 235000018734 Sambucus australis Nutrition 0.000 claims description 8
- 244000180577 Sambucus australis Species 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- -1 9a-aza-9a-homoerythromycin compound Chemical class 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 208000023275 Autoimmune disease Diseases 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 206010061218 Inflammation Diseases 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 238000005915 ammonolysis reaction Methods 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000028993 immune response Effects 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 238000007142 ring opening reaction Methods 0.000 claims description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 3
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 238000010931 ester hydrolysis Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 claims description 3
- WRVHPSSSTBDGRK-UHFFFAOYSA-N sodium;sulfane;hydrate Chemical compound O.[Na].S WRVHPSSSTBDGRK-UHFFFAOYSA-N 0.000 claims description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 claims description 2
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims description 2
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 238000006969 Curtius rearrangement reaction Methods 0.000 claims description 2
- 239000002841 Lewis acid Substances 0.000 claims description 2
- 229910010082 LiAlH Inorganic materials 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 2
- 125000005217 alkenylheteroaryl group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims description 2
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000007822 coupling agent Substances 0.000 claims description 2
- 150000004292 cyclic ethers Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 2
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims description 2
- 150000007517 lewis acids Chemical class 0.000 claims description 2
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 2
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 claims description 2
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 claims description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 238000007248 oxidative elimination reaction Methods 0.000 claims description 2
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims description 2
- 230000008707 rearrangement Effects 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910000077 silane Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- XBGUDOLPBJYSNA-UHFFFAOYSA-N sodium;trimethyl(sulfido)silane Chemical compound [Na+].C[Si](C)(C)[S-] XBGUDOLPBJYSNA-UHFFFAOYSA-N 0.000 claims description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 claims description 2
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- XNFVGEUMTFIVHQ-UHFFFAOYSA-N disodium;sulfide;hydrate Chemical compound O.[Na+].[Na+].[S-2] XNFVGEUMTFIVHQ-UHFFFAOYSA-N 0.000 claims 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 description 39
- 230000005764 inhibitory process Effects 0.000 description 4
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
- 238000012261 overproduction Methods 0.000 description 2
- UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1608236.4 | 2016-05-11 | ||
| GBGB1608236.4A GB201608236D0 (en) | 2016-05-11 | 2016-05-11 | Seco macrolide compounds |
| PCT/EP2017/060889 WO2017194452A1 (en) | 2016-05-11 | 2017-05-08 | Seco macrolide compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019515014A JP2019515014A (ja) | 2019-06-06 |
| JP2019515014A5 true JP2019515014A5 (enExample) | 2020-06-25 |
| JP7112963B2 JP7112963B2 (ja) | 2022-08-04 |
Family
ID=56297499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018559881A Active JP7112963B2 (ja) | 2016-05-11 | 2017-05-08 | セコマクロライド化合物 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US10919910B2 (enExample) |
| EP (1) | EP3455234A1 (enExample) |
| JP (1) | JP7112963B2 (enExample) |
| CN (1) | CN109311929B (enExample) |
| AU (2) | AU2017262706B9 (enExample) |
| CA (1) | CA3024324A1 (enExample) |
| GB (1) | GB201608236D0 (enExample) |
| SG (2) | SG10202111097TA (enExample) |
| WO (1) | WO2017194452A1 (enExample) |
| ZA (1) | ZA201807297B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110669930A (zh) * | 2019-09-23 | 2020-01-10 | 中国科学院青海盐湖研究所 | 用于分离高镁锂比溶液中锂的复合萃取剂以及萃取方法 |
| JP7495758B2 (ja) * | 2020-01-08 | 2024-06-05 | ベイジン コンティネント ファーマシューティカルズ カンパニー，リミテッド | マクロライド化合物及びその慢性呼吸器疾患の治療用途 |
| US11771677B2 (en) * | 2020-03-12 | 2023-10-03 | Zoetis Services Llc | Immunomodulating urea azalides |
| CA3231535A1 (en) * | 2021-09-07 | 2023-03-16 | Zoetis Services Llc | Immunomodulating azalides |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3725385A (en) | 1970-11-02 | 1973-04-03 | Abbott Lab | Process for the demethylation of 3-amino macrolides |
| EP0283055B1 (en) * | 1987-09-03 | 1990-08-29 | SOUR PLIVA farmaceutska, Kemijska prehrambena i kozmeticka industrija, n.sol.o. | 10-dihydro-10-deoxo-11-azaerythronolide-a-compounds, methods and intermediates for the manufacture thereof and their use in pharmaceuticals and in the manufacture thereof |
| SI8911498B (sl) * | 1989-07-26 | 1998-10-31 | Pliva | Postopek za pripravo derivatov tilozina |
| SI9011409A (en) | 1990-07-18 | 1995-10-31 | Pliva Pharm & Chem Works | O-methyl azitromycin derivates, methods and intermediates for their preparation and methods for preparation of pharmaceuticals products which comprise them |
| CA2065222A1 (en) | 1991-04-09 | 1992-10-10 | Robert R. Wilkening | Process for the preparation of 8a-aza-8a-homoerythromycin cyclic iminoethers |
| US5215980A (en) * | 1992-01-17 | 1993-06-01 | Merck & Co., Inc. | 10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof |
| GB2270072A (en) * | 1992-09-01 | 1994-03-02 | Merck & Co Inc | Tetrahydropyran compounds |
| HRP950145A2 (en) * | 1995-03-27 | 1997-08-31 | Sour Pliva | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
| IT1306205B1 (it) | 1999-01-15 | 2001-05-30 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| HRP990116B1 (en) | 1999-04-20 | 2007-10-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | NOVEL 8a AND 9a- 15-MEMBERED LACTAMES |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| NZ537717A (en) | 2002-07-08 | 2006-04-28 | Pliva Istrazivacki Inst D | New compounds, compositions and methods for treatment of inflammatory diseases and conditions |
| ITMI20021726A1 (it) | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| HRP20020779A2 (en) | 2002-09-27 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | NEW 3-DECLADINOSYL DERIVATIVES OF 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHROMICIN A 9a, 11-CYCLIC CARBAMATES |
| HRP20030381B1 (en) | 2003-05-14 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | 3-DECLADINOZYL 9a-N-CARBAMOYL AND 9a-N-THIOCARBAMOYL DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHROMICYNE A |
| US7435805B2 (en) | 2003-05-30 | 2008-10-14 | Glaxpsmithkline Istrazivacki | O-alkyl macrolide and azalide derivatives and regioselective process for their preparation |
| MXPA06012923A (es) | 2004-05-06 | 2007-07-18 | Glaxosmithkline Zagreb | Macrolidos asociados a ester utiles para el tratamiento de infecciones microbianas. |
| CN105246334A (zh) | 2013-04-04 | 2016-01-13 | 哈佛大学的校长及成员们 | 大环内酯及其制备和使用方法 |
-
2016
- 2016-05-11 GB GBGB1608236.4A patent/GB201608236D0/en not_active Ceased
-
2017
- 2017-05-08 JP JP2018559881A patent/JP7112963B2/ja active Active
- 2017-05-08 CN CN201780028758.8A patent/CN109311929B/zh active Active
- 2017-05-08 US US16/300,495 patent/US10919910B2/en active Active
- 2017-05-08 SG SG10202111097TA patent/SG10202111097TA/en unknown
- 2017-05-08 WO PCT/EP2017/060889 patent/WO2017194452A1/en not_active Ceased
- 2017-05-08 EP EP17724517.2A patent/EP3455234A1/en active Pending
- 2017-05-08 AU AU2017262706A patent/AU2017262706B9/en active Active
- 2017-05-08 CA CA3024324A patent/CA3024324A1/en active Pending
- 2017-05-08 SG SG11201809989XA patent/SG11201809989XA/en unknown
-
2018
- 2018-10-31 ZA ZA2018/07297A patent/ZA201807297B/en unknown
-
2020
- 2020-12-24 US US17/133,979 patent/US11512096B2/en active Active
-
2021
- 2021-03-02 AU AU2021201355A patent/AU2021201355B2/en active Active
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