CA2564249A1 - Indole and azaindole derivatives with antitumor action - Google Patents
Indole and azaindole derivatives with antitumor action Download PDFInfo
- Publication number
- CA2564249A1 CA2564249A1 CA002564249A CA2564249A CA2564249A1 CA 2564249 A1 CA2564249 A1 CA 2564249A1 CA 002564249 A CA002564249 A CA 002564249A CA 2564249 A CA2564249 A CA 2564249A CA 2564249 A1 CA2564249 A1 CA 2564249A1
- Authority
- CA
- Canada
- Prior art keywords
- dimethoxy
- indole
- phenyl
- methoxyphenyl
- carboxylic acid
- 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
- 230000000259 anti-tumor effect Effects 0.000 title abstract description 22
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 16
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract description 8
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract description 8
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 232
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 42
- 239000003814 drug Substances 0.000 claims abstract description 26
- 229940079593 drug Drugs 0.000 claims abstract description 25
- 229940041181 antineoplastic drug Drugs 0.000 claims abstract description 15
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
- -1 hydroxypropyl Chemical group 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 150000002148 esters Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 8
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 8
- 150000001408 amides Chemical group 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- 238000002560 therapeutic procedure Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000000725 suspension Substances 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 5
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 5
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 4
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical group 0.000 claims description 4
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 239000008187 granular material Substances 0.000 claims description 3
- HCUARRIEZVDMPT-UHFFFAOYSA-N indolyl-2-carboxylic acid Natural products C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000006188 syrup Substances 0.000 claims description 3
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- AEIDURNZWCNQIM-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrazino[1,2-a]indole Chemical class C1=CC=C2N3CCNCC3=CC2=C1 AEIDURNZWCNQIM-UHFFFAOYSA-N 0.000 claims description 2
- XBNNAWXSOZXJGU-UHFFFAOYSA-N 2,4-dihydro-1h-pyrazino[1,2-a]indol-3-one Chemical class C1=CC=C2N3CC(=O)NCC3=CC2=C1 XBNNAWXSOZXJGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- HVZAFNRIZAKUQS-UHFFFAOYSA-N 3,4-dihydro-1h-[1,4]oxazino[4,3-a]indole Chemical class C1=CC=C2N3CCOCC3=CC2=C1 HVZAFNRIZAKUQS-UHFFFAOYSA-N 0.000 claims description 2
- KRRWBFJXTNMYOZ-UHFFFAOYSA-N 3,4-dihydro-2h-pyrazino[1,2-a]indol-1-one Chemical class C1=CC=C2N3CCNC(=O)C3=CC2=C1 KRRWBFJXTNMYOZ-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 2
- 229940045985 antineoplastic platinum compound Drugs 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
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- 239000007902 hard capsule Substances 0.000 claims description 2
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 2
- 238000001802 infusion Methods 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- JQORPSVTMQXKID-UHFFFAOYSA-N methyl 5,6-dimethoxy-3-(4-methoxyphenyl)-1-(2-pyrrolidin-1-ylethyl)indole-2-carboxylate;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2N(CCN2CCCC2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 JQORPSVTMQXKID-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000843 powder Substances 0.000 claims description 2
- 238000001959 radiotherapy Methods 0.000 claims description 2
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- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- KAAZZEBFTFXGJQ-UHFFFAOYSA-N 7,8-dimethoxy-10-(4-methoxyphenyl)-n-methyl-3,4-dihydro-1h-pyrazino[1,2-a]indole-2-carboxamide Chemical compound C1N(C(=O)NC)CCN(C2=CC(OC)=C(OC)C=C22)C1=C2C1=CC=C(OC)C=C1 KAAZZEBFTFXGJQ-UHFFFAOYSA-N 0.000 claims 1
- RSWFMUPFLONLLK-UHFFFAOYSA-N 7,8-dimethoxy-10-phenyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole;hydrochloride Chemical compound Cl.C=12CNCCN2C=2C=C(OC)C(OC)=CC=2C=1C1=CC=CC=C1 RSWFMUPFLONLLK-UHFFFAOYSA-N 0.000 claims 1
- 239000002257 antimetastatic agent Substances 0.000 claims 1
- RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims 1
- 229940102223 injectable solution Drugs 0.000 claims 1
- 239000003094 microcapsule Substances 0.000 claims 1
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- 238000000034 method Methods 0.000 abstract description 62
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 205
- 238000005160 1H NMR spectroscopy Methods 0.000 description 79
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 71
- 239000000243 solution Substances 0.000 description 69
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 65
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
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- 239000007832 Na2SO4 Substances 0.000 description 32
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
- 229910052938 sodium sulfate Inorganic materials 0.000 description 32
- 235000011152 sodium sulphate Nutrition 0.000 description 32
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
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- HKYLCXWKYSZDBP-UHFFFAOYSA-N ethyl 5,6-dimethoxy-3-pyridin-4-yl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=NC=C1 HKYLCXWKYSZDBP-UHFFFAOYSA-N 0.000 description 1
- FSLOLRKVZPTMHC-UHFFFAOYSA-N ethyl 5-chloro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 FSLOLRKVZPTMHC-UHFFFAOYSA-N 0.000 description 1
- XBBONQKRNZIXTH-UHFFFAOYSA-N ethyl 5-fluoro-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(F)C=C2C=1C1=CC=CC=C1 XBBONQKRNZIXTH-UHFFFAOYSA-N 0.000 description 1
- LLBDOBISQBECLH-UHFFFAOYSA-N ethyl 5-hydroxy-3-phenyl-1h-indole-2-carboxylate Chemical compound CCOC(=O)C=1NC2=CC=C(O)C=C2C=1C1=CC=CC=C1 LLBDOBISQBECLH-UHFFFAOYSA-N 0.000 description 1
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- LIYGYAHYXQDGEP-UHFFFAOYSA-N firefly oxyluciferin Natural products Oc1csc(n1)-c1nc2ccc(O)cc2s1 LIYGYAHYXQDGEP-UHFFFAOYSA-N 0.000 description 1
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- PIFNRGUHVQRYKQ-UHFFFAOYSA-N methyl 1-benzyl-5,6-dimethoxy-3-(4-methoxyphenyl)indole-2-carboxylate Chemical compound C12=CC(OC)=C(OC)C=C2N(CC=2C=CC=CC=2)C(C(=O)OC)=C1C1=CC=C(OC)C=C1 PIFNRGUHVQRYKQ-UHFFFAOYSA-N 0.000 description 1
- NQPIEWBAWBFGOB-UHFFFAOYSA-N methyl 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)OC)=CC2=C1 NQPIEWBAWBFGOB-UHFFFAOYSA-N 0.000 description 1
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- RWBHWSUJSFZICA-UHFFFAOYSA-N methyl 3-(4-fluorophenyl)-5,6-dimethoxy-1h-indole-2-carboxylate Chemical compound COC(=O)C=1NC2=CC(OC)=C(OC)C=C2C=1C1=CC=C(F)C=C1 RWBHWSUJSFZICA-UHFFFAOYSA-N 0.000 description 1
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- 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
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- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 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
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- FCFNRCROJUBPLU-DNDCDFAISA-N valinomycin Chemical compound CC(C)[C@@H]1NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC(=O)[C@H](C(C)C)NC(=O)[C@H](C)OC(=O)[C@@H](C(C)C)NC(=O)[C@@H](C(C)C)OC1=O FCFNRCROJUBPLU-DNDCDFAISA-N 0.000 description 1
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Classifications
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
-
- 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
- A61K31/28—Compounds containing heavy metals
- A61K31/282—Platinum compounds
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/337—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having four-membered rings, e.g. taxol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2004A000874 | 2004-04-30 | ||
| IT000874A ITMI20040874A1 (it) | 2004-04-30 | 2004-04-30 | Derivati indolici ed azaindolici con azione antitumorale |
| PCT/EP2005/051908 WO2005105213A2 (en) | 2004-04-30 | 2005-04-27 | Indole and azaindole derivatives with antitumor action |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2564249A1 true CA2564249A1 (en) | 2005-11-10 |
Family
ID=34968098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002564249A Abandoned CA2564249A1 (en) | 2004-04-30 | 2005-04-27 | Indole and azaindole derivatives with antitumor action |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20070248672A1 (enExample) |
| EP (1) | EP1750687A2 (enExample) |
| JP (1) | JP2007535520A (enExample) |
| AU (1) | AU2005237788A1 (enExample) |
| CA (1) | CA2564249A1 (enExample) |
| IT (1) | ITMI20040874A1 (enExample) |
| WO (1) | WO2005105213A2 (enExample) |
Families Citing this family (37)
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| WO2005095400A1 (en) | 2004-03-30 | 2005-10-13 | Vertex Pharmaceuticals Incorporated | Azaindoles useful as inhibitors of jak and other protein kinases |
| EP1779848A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of inflammatory and autoimmune diseases |
| EP1779849A1 (en) * | 2005-10-28 | 2007-05-02 | Nikem Research S.R.L. | V-ATPase inhibitors for the treatment of septic shock |
| JP2010503677A (ja) | 2006-09-15 | 2010-02-04 | シェーリング コーポレイション | 脂質代謝の障害を治療するためのアゼチジノン誘導体 |
| CN101678022A (zh) | 2006-12-21 | 2010-03-24 | 弗特克斯药品有限公司 | 可用作蛋白激酶抑制剂的5-氰基-4-(吡咯并[2,3b]吡啶-3-基)嘧啶衍生物 |
| US20100183658A1 (en) * | 2007-03-30 | 2010-07-22 | The Brigham And Women's Hospital, Inc. | Novel Compounds for Enhancing MHC Class II Therapies |
| CA2951295C (en) * | 2007-04-16 | 2020-04-28 | Abbvie Inc. | 7-nonsubstituted indole mcl-1 inhibitors |
| WO2010144611A2 (en) * | 2009-06-10 | 2010-12-16 | 3-V Biosciences, Inc. | Antivirals that target transporters, carriers, and ion channels |
| AU2010262905B2 (en) | 2009-06-17 | 2015-04-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| JP5687704B2 (ja) * | 2009-10-07 | 2015-03-18 | カロ バイオ アクチェブラーグ | 新規エストロゲン受容体リガンド |
| HRP20161092T1 (hr) | 2010-10-25 | 2016-10-21 | G1 Therapeutics, Inc. | Cdk inhibitori |
| US8691830B2 (en) | 2010-10-25 | 2014-04-08 | G1 Therapeutics, Inc. | CDK inhibitors |
| KR20140014110A (ko) | 2010-12-16 | 2014-02-05 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| GB201113538D0 (en) | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| AU2013232066B2 (en) | 2012-03-16 | 2017-07-06 | Vitae Pharmaceuticals, Inc. | Liver X receptor modulators |
| LT2825542T (lt) | 2012-03-16 | 2016-12-27 | Vitae Pharmaceuticals, Inc. | Kepenų x receptoriaus moduliatoriai |
| CA2868966C (en) | 2012-03-29 | 2021-01-26 | Francis Xavier Tavares | Lactam kinase inhibitors |
| ES2734479T3 (es) * | 2012-09-21 | 2019-12-10 | Vivolux Ab | Medios y métodos para tratar tumores sólidos |
| WO2014144326A1 (en) | 2013-03-15 | 2014-09-18 | G1 Therapeutics, Inc. | Transient protection of normal cells during chemotherapy |
| CN105407723A (zh) | 2013-03-15 | 2016-03-16 | G1治疗公司 | 高效的抗赘生剂和抗增生剂 |
| MA38569A1 (fr) * | 2013-04-23 | 2017-03-31 | Esteve Labor Dr | Composés pyrazino[1,2-a]indole, leur préparation et utilisation dans des médicaments |
| ES2741444T3 (es) | 2013-11-13 | 2020-02-11 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| EP3068782B1 (en) | 2013-11-13 | 2018-05-23 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| US20150297606A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic Lactams for Use in the Protection of Hematopoietic Stem and Progenitor Cells Against Ionizing Radiation |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| WO2016040858A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| MX389753B (es) * | 2015-06-17 | 2025-03-20 | Pfizer | Compuestos triciclicos y su uso como inhibidores de la fosfodiesterasa |
| US11866409B2 (en) | 2015-11-02 | 2024-01-09 | Carmel-Haifa University Economic Corporation Ltd. | Apoptosis related protein in the tgf-beta signaling pathway (ARTS) mimetic compounds, compositions, methods and uses thereof in induction of differentiation and/or apoptosis of premalignant and malignant cells, thereby restoring their normal-like phenotype |
| GB201521059D0 (en) | 2015-11-30 | 2016-01-13 | Isis Innovation | Inhibitors of metallo-beta-lactamases |
| EP3565558B1 (en) | 2017-01-06 | 2023-12-06 | G1 Therapeutics, Inc. | Combination therapy with a serd compound and a cdk4/6 inhibitor for the treatment of cancer |
| WO2019006393A1 (en) | 2017-06-29 | 2019-01-03 | G1 Therapeutics, Inc. | Morphic forms of git38 and methods of manufacture thereof |
| KR20210049847A (ko) | 2018-08-24 | 2021-05-06 | 쥐원 쎄라퓨틱스, 인크. | 1,4-디아자스피로[5.5]운데칸-3-온의 개선된 합성 |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| UY39579A (es) | 2020-12-22 | 2022-07-29 | Novartis Ag | COMPUESTOS Y COMPOSICIÓN PARA EL TRATAMIENTO DE CONDICIONES ASOCIADAS CON cGAS |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US105140A (en) * | 1870-07-05 | Improvement in cigar-wrapping machines | ||
| DE2005845A1 (de) * | 1969-02-12 | 1970-09-03 | Sumitomo Chemical Company, Ltd., Osaka (Japan) | Verfahren zur Herstellung von Benzodiazepinen und ihren Salzen |
| CA1012147A (en) * | 1972-09-25 | 1977-06-14 | Hoffmann-La Roche Limited | Indolo quinoline derivatives |
| AR205437A1 (es) * | 1972-09-25 | 1976-05-07 | Hoffmann La Roche | Procedimiento para la preparacion de derivados de indoloquinolinona |
| US4225711A (en) * | 1978-10-02 | 1980-09-30 | Schering Corporation | Substituted 2-[(methylsulfinyl)acetyl]-3-heterocyclicindoles and their use as immunosuppressants |
| CA2038925A1 (en) * | 1990-03-26 | 1991-09-27 | Takashi Sohda | Indole derivatives, their production and use |
| JPH04211651A (ja) * | 1990-03-26 | 1992-08-03 | Takeda Chem Ind Ltd | 骨吸収抑制剤およびインドール誘導体 |
| GB9319100D0 (en) * | 1993-09-15 | 1993-11-03 | Pfizer Ltd | 3-(3-pyridinyl)h-indoles |
| JP2001122855A (ja) * | 1999-10-27 | 2001-05-08 | Japan Tobacco Inc | インドール化合物及びその医薬用途 |
| US6323228B1 (en) * | 2000-09-15 | 2001-11-27 | Abbott Laboratories | 3-substituted indole angiogenesis inhibitors |
| US20020128292A1 (en) * | 2000-12-07 | 2002-09-12 | Cai Sui Xiong | Substituted indole-2-carboxylic acid benzylidene-hydrazides and analogs as activators of caspases and inducers of apoptosis and the use thereof |
| AU2002302248B2 (en) * | 2001-05-23 | 2008-03-06 | Merck Frosst Canada Ltd. | Dihydropyrrolo[1,2-A]indole and tetrahydropyrido[1,2-A]-indole derivatives as prostaglandin D2 receptor antagonists |
| DE10155076A1 (de) * | 2001-11-09 | 2003-05-22 | Merck Patent Gmbh | Verwendung von Endothelin-Rezeptor-Antagonisten zur Behandlung von Tumorerkrankungen |
| US7268159B2 (en) * | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
-
2004
- 2004-04-30 IT IT000874A patent/ITMI20040874A1/it unknown
-
2005
- 2005-04-27 WO PCT/EP2005/051908 patent/WO2005105213A2/en not_active Ceased
- 2005-04-27 AU AU2005237788A patent/AU2005237788A1/en not_active Abandoned
- 2005-04-27 US US11/579,237 patent/US20070248672A1/en not_active Abandoned
- 2005-04-27 EP EP05743013A patent/EP1750687A2/en not_active Withdrawn
- 2005-04-27 JP JP2007510035A patent/JP2007535520A/ja active Pending
- 2005-04-27 CA CA002564249A patent/CA2564249A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007535520A (ja) | 2007-12-06 |
| WO2005105213A3 (en) | 2006-06-22 |
| WO2005105213A2 (en) | 2005-11-10 |
| ITMI20040874A1 (it) | 2004-07-30 |
| EP1750687A2 (en) | 2007-02-14 |
| AU2005237788A1 (en) | 2005-11-10 |
| US20070248672A1 (en) | 2007-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |