ES2707099T3 - Novedosos compuestos de imidazobenzotiazol fusionados - Google Patents
Novedosos compuestos de imidazobenzotiazol fusionados Download PDFInfo
- Publication number
- ES2707099T3 ES2707099T3 ES15717242T ES15717242T ES2707099T3 ES 2707099 T3 ES2707099 T3 ES 2707099T3 ES 15717242 T ES15717242 T ES 15717242T ES 15717242 T ES15717242 T ES 15717242T ES 2707099 T3 ES2707099 T3 ES 2707099T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- tert
- butyl
- benzothiazole
- imidazo
- 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.)
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- HWAXRLFNEXLBSN-UHFFFAOYSA-N 2h-imidazo[4,5-g][1,3]benzothiazole Chemical class C1=CC2=NCSC2=C2N=CN=C21 HWAXRLFNEXLBSN-UHFFFAOYSA-N 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 272
- -1 carbocycle (C3-C10) Chemical group 0.000 claims abstract description 129
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 114
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 57
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 44
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 125000001424 substituent group Chemical group 0.000 claims abstract description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 15
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 9
- 150000004677 hydrates Chemical class 0.000 claims abstract description 7
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims abstract description 6
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003003 spiro group Chemical group 0.000 claims abstract description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 8
- 229910004727 OSO3H Inorganic materials 0.000 claims abstract 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 44
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 37
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 30
- KYUNTDRHCPSMOG-UHFFFAOYSA-N 2h-1,3-benzothiazole-3-carboxylic acid Chemical compound C1=CC=C2N(C(=O)O)CSC2=C1 KYUNTDRHCPSMOG-UHFFFAOYSA-N 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 208000006673 asthma Diseases 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 230000000172 allergic effect Effects 0.000 claims description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- YDSIWJMQLZGKPN-UHFFFAOYSA-N ethyl 2h-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)CSC2=C1 YDSIWJMQLZGKPN-UHFFFAOYSA-N 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 9
- LYASTVLDAJIXBL-UHFFFAOYSA-N 1,3-benzothiazole-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=NC2=C1 LYASTVLDAJIXBL-UHFFFAOYSA-N 0.000 claims description 8
- SZXLBDVCHABEGD-UHFFFAOYSA-N 2h-1,3-benzothiazole-3-carboxamide Chemical compound C1=CC=C2N(C(=O)N)CSC2=C1 SZXLBDVCHABEGD-UHFFFAOYSA-N 0.000 claims description 8
- 208000010668 atopic eczema Diseases 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- 208000028004 allergic respiratory disease Diseases 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- JAORDPHDFCRJHV-UHFFFAOYSA-N C(C)(C)(C)C1=NN(C(=C1)NC(=O)NCC1=C(C=CC=C1)OC1=CC2=C(N3C(S2)=NC=C3CN3CCOCC3)C=C1)C1=CC(=C(C=C1)O)Cl Chemical compound C(C)(C)(C)C1=NN(C(=C1)NC(=O)NCC1=C(C=CC=C1)OC1=CC2=C(N3C(S2)=NC=C3CN3CCOCC3)C=C1)C1=CC(=C(C=C1)O)Cl JAORDPHDFCRJHV-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 208000037915 non-allergic respiratory disease Diseases 0.000 claims description 4
- JFUXAVXBKOSDQG-UHFFFAOYSA-N CCOC(=O)C1=CN=C2SC3=CC(SC4=CC=C(N)C=C4)=CC=C3N12 Chemical compound CCOC(=O)C1=CN=C2SC3=CC(SC4=CC=C(N)C=C4)=CC=C3N12 JFUXAVXBKOSDQG-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- VHCYCGCLVHHYOV-UHFFFAOYSA-N methyl 2h-1,3-benzothiazole-3-carboxylate Chemical compound C1=CC=C2N(C(=O)OC)CSC2=C1 VHCYCGCLVHHYOV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 7
- 239000005977 Ethylene Substances 0.000 claims 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 6
- 208000018569 Respiratory Tract disease Diseases 0.000 claims 2
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 claims 2
- CXSZJIQQHGTRKT-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]-3-[[2-[1-(5-methyl-1,3-oxazol-2-yl)imidazo[2,1-b][1,3]benzothiazol-6-yl]oxyphenyl]methyl]urea Chemical compound CC1=CN=C(O1)C1=CN=C2SC3=CC(OC4=C(CNC(=O)NC5=CC(=NN5C5=CC(Cl)=C(O)C=C5)C(C)(C)C)C=CC=C4)=CC=C3N12 CXSZJIQQHGTRKT-UHFFFAOYSA-N 0.000 claims 1
- SXXRLLAFGUNUBO-UHFFFAOYSA-N 1-[5-tert-butyl-2-(3-chloro-4-hydroxyphenyl)pyrazol-3-yl]-3-[[2-[1-(ethoxymethyl)imidazo[2,1-b][1,3]benzothiazol-6-yl]oxyphenyl]methyl]urea Chemical compound C(C)(C)(C)C1=NN(C(=C1)NC(=O)NCC1=C(C=CC=C1)OC1=CC2=C(N3C(S2)=NC=C3COCC)C=C1)C1=CC(=C(C=C1)O)Cl SXXRLLAFGUNUBO-UHFFFAOYSA-N 0.000 claims 1
- AKWIAIDKXNKXDI-UHFFFAOYSA-N 1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C=CNC=1 AKWIAIDKXNKXDI-UHFFFAOYSA-N 0.000 claims 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- HXLRNOPOSHUGOM-UHFFFAOYSA-N CCOC(=O)C1=CN=C2SC3=CC(OC4=CC=C(C=C4)[N+]([O-])=O)=CC=C3N12 Chemical compound CCOC(=O)C1=CN=C2SC3=CC(OC4=CC=C(C=C4)[N+]([O-])=O)=CC=C3N12 HXLRNOPOSHUGOM-UHFFFAOYSA-N 0.000 claims 1
- PMCBOYXSWVLAKS-UHFFFAOYSA-N CCOC(=O)C1=CN=C2SC3=CC(SC4=CC=C(C=C4)[N+]([O-])=O)=CC=C3N12 Chemical compound CCOC(=O)C1=CN=C2SC3=CC(SC4=CC=C(C=C4)[N+]([O-])=O)=CC=C3N12 PMCBOYXSWVLAKS-UHFFFAOYSA-N 0.000 claims 1
- VYKARAJFDCVNBX-UHFFFAOYSA-N COCCO.NC(=O)N Chemical compound COCCO.NC(=O)N VYKARAJFDCVNBX-UHFFFAOYSA-N 0.000 claims 1
- 101100456896 Drosophila melanogaster metl gene Proteins 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 claims 1
- RSOJSFYJLQADDM-UHFFFAOYSA-N ethanesulfonamide Chemical compound [CH2]CS(N)(=O)=O RSOJSFYJLQADDM-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000005157 alkyl carboxy group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 57
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- 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 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000002877 time resolved fluorescence resonance energy transfer Methods 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
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005310 triazolidinyl group Chemical group N1(NNCC1)* 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1089MU2014 | 2014-03-27 | ||
| PCT/IB2015/052124 WO2015145336A1 (en) | 2014-03-27 | 2015-03-24 | Novel fused imidazobenzothiazole compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2707099T3 true ES2707099T3 (es) | 2019-04-02 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15717242T Active ES2707099T3 (es) | 2014-03-27 | 2015-03-24 | Novedosos compuestos de imidazobenzotiazol fusionados |
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| AR (1) | AR099867A1 (enExample) |
| AU (1) | AU2015237840B2 (enExample) |
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| CY (1) | CY1121147T1 (enExample) |
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| IL (1) | IL247955B (enExample) |
| LT (1) | LT3122755T (enExample) |
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| MY (1) | MY193041A (enExample) |
| PH (1) | PH12016501903B1 (enExample) |
| PL (1) | PL3122755T3 (enExample) |
| PT (1) | PT3122755T (enExample) |
| RS (1) | RS58324B1 (enExample) |
| SG (1) | SG11201607793RA (enExample) |
| SI (1) | SI3122755T1 (enExample) |
| SM (1) | SMT201900036T1 (enExample) |
| TR (1) | TR201900735T4 (enExample) |
| TW (1) | TWI648282B (enExample) |
| UA (1) | UA121469C2 (enExample) |
| WO (1) | WO2015145336A1 (enExample) |
| ZA (1) | ZA201606598B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
| EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| TWI648282B (zh) * | 2014-03-27 | 2019-01-21 | 印度商托仁特生技有限公司 | 新熔合咪唑苯并噻唑化合物 |
| DE102016209204A1 (de) | 2016-05-27 | 2017-11-30 | Robert Bosch Gmbh | Vorrichtung zur Regelung mindestens eines Fluidstroms in einem Fahrzeug |
| KR102630959B1 (ko) * | 2016-10-31 | 2024-01-29 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치 |
| CN106727538A (zh) * | 2017-02-20 | 2017-05-31 | 潘连香 | 一种治疗2型糖尿病的药物组合物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8724566D0 (en) | 1987-10-20 | 1987-11-25 | Roussel Lab Ltd | Chemical compounds |
| GB8908845D0 (en) | 1989-04-19 | 1989-06-07 | Roussel Lab Ltd | Chemical compounds |
| WO1995029922A1 (en) * | 1994-04-29 | 1995-11-09 | Pharmacia & Upjohn Company | Methanol derivatives for treatment of retroviral infections especially hiv infections |
| WO2002014321A1 (en) | 2000-08-11 | 2002-02-21 | The Regents Of The University Of California | Use of stat-6 inhibitors as therapeutic agents |
| US7601846B2 (en) * | 2001-06-26 | 2009-10-13 | The Regents Of The University Of California | Compounds having activity as inhibitors of apoptosis |
| CA2506796A1 (en) * | 2002-11-25 | 2004-06-10 | Pharmacia Corporation | Heteroarylsulfonylmethyl hydroxamic acids and amides and their use as protease inhibitors |
| GB0320244D0 (en) * | 2003-05-06 | 2003-10-01 | Aventis Pharma Inc | Pyrazoles as inhibitors of tumour necrosis factor |
| JP2009526037A (ja) * | 2006-02-09 | 2009-07-16 | ファイザー・リミテッド | トリアゾロピリジン化合物 |
| TWI648282B (zh) * | 2014-03-27 | 2019-01-21 | 印度商托仁特生技有限公司 | 新熔合咪唑苯并噻唑化合物 |
-
2015
- 2015-03-16 TW TW104108329A patent/TWI648282B/zh not_active IP Right Cessation
- 2015-03-24 ES ES15717242T patent/ES2707099T3/es active Active
- 2015-03-24 HU HUE15717242A patent/HUE042493T2/hu unknown
- 2015-03-24 LT LTEP15717242.0T patent/LT3122755T/lt unknown
- 2015-03-24 HR HRP20190121TT patent/HRP20190121T1/hr unknown
- 2015-03-24 SI SI201530555T patent/SI3122755T1/sl unknown
- 2015-03-24 WO PCT/IB2015/052124 patent/WO2015145336A1/en not_active Ceased
- 2015-03-24 PT PT15717242T patent/PT3122755T/pt unknown
- 2015-03-24 US US15/128,886 patent/US9908898B2/en active Active
- 2015-03-24 SM SM20190036T patent/SMT201900036T1/it unknown
- 2015-03-24 SG SG11201607793RA patent/SG11201607793RA/en unknown
- 2015-03-24 EP EP15717242.0A patent/EP3122755B1/en active Active
- 2015-03-24 AU AU2015237840A patent/AU2015237840B2/en not_active Ceased
- 2015-03-24 PL PL15717242T patent/PL3122755T3/pl unknown
- 2015-03-24 UA UAA201610628A patent/UA121469C2/uk unknown
- 2015-03-24 EA EA201691920A patent/EA029745B9/ru not_active IP Right Cessation
- 2015-03-24 CA CA2943098A patent/CA2943098C/en active Active
- 2015-03-24 MY MYPI2016703533A patent/MY193041A/en unknown
- 2015-03-24 MX MX2016012535A patent/MX368985B/es active IP Right Grant
- 2015-03-24 RS RS20190084A patent/RS58324B1/sr unknown
- 2015-03-24 JP JP2016559356A patent/JP6480949B2/ja not_active Expired - Fee Related
- 2015-03-24 KR KR1020167029134A patent/KR102339610B1/ko not_active Expired - Fee Related
- 2015-03-24 CN CN201580024068.6A patent/CN106414458B/zh not_active Expired - Fee Related
- 2015-03-24 DK DK15717242.0T patent/DK3122755T3/en active
- 2015-03-24 TR TR2019/00735T patent/TR201900735T4/tr unknown
- 2015-03-27 AR ARP150100915A patent/AR099867A1/es not_active Application Discontinuation
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2016
- 2016-09-21 IL IL247955A patent/IL247955B/en active IP Right Grant
- 2016-09-23 ZA ZA2016/06598A patent/ZA201606598B/en unknown
- 2016-09-27 PH PH12016501903A patent/PH12016501903B1/en unknown
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2018
- 2018-01-03 US US15/861,399 patent/US10227361B2/en active Active
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2019
- 2019-01-21 CY CY20191100076T patent/CY1121147T1/el unknown
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