AU2006297124B2 - 2-amino-7,8-dihydro-6H-pyrido(4,3-d) pyrimidin-5-ones - Google Patents
2-amino-7,8-dihydro-6H-pyrido(4,3-d) pyrimidin-5-ones Download PDFInfo
- Publication number
- AU2006297124B2 AU2006297124B2 AU2006297124A AU2006297124A AU2006297124B2 AU 2006297124 B2 AU2006297124 B2 AU 2006297124B2 AU 2006297124 A AU2006297124 A AU 2006297124A AU 2006297124 A AU2006297124 A AU 2006297124A AU 2006297124 B2 AU2006297124 B2 AU 2006297124B2
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- Australia
- Prior art keywords
- phenyl
- methoxy
- methyl
- pyridin
- fluoro
- 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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- CZOQBGHFZWUWPV-UHFFFAOYSA-N 2-amino-7,8-dihydro-6h-pyrido[4,3-d]pyrimidin-5-one Chemical class O=C1NCCC2=NC(N)=NC=C21 CZOQBGHFZWUWPV-UHFFFAOYSA-N 0.000 title abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 83
- 229940002612 prodrug Drugs 0.000 claims abstract description 75
- 239000000651 prodrug Substances 0.000 claims abstract description 75
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 238000000034 method Methods 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 28
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 201000010099 disease Diseases 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 16
- 230000003612 virological effect Effects 0.000 claims abstract description 14
- 239000003937 drug carrier Substances 0.000 claims abstract description 7
- -1 2-methyl-2 morpholinopropyl Chemical group 0.000 claims description 940
- 150000001875 compounds Chemical class 0.000 claims description 193
- 125000000217 alkyl group Chemical group 0.000 claims description 105
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 91
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
- 125000001072 heteroaryl group Chemical group 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 206010028980 Neoplasm Diseases 0.000 claims description 44
- 125000005843 halogen group Chemical group 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
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- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 23
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 19
- 125000000335 thiazolyl group Chemical group 0.000 claims description 18
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- 125000001544 thienyl group Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 15
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
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- 241001465754 Metazoa Species 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
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- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
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- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 9
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 8
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 8
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 8
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
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- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 8
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 7
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 7
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- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 7
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 7
- 201000001441 melanoma Diseases 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
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- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 6
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- RRXSYZFVDIRTFB-UHFFFAOYSA-N C[CH]C1=CC=C(OC)C=C1 Chemical group C[CH]C1=CC=C(OC)C=C1 RRXSYZFVDIRTFB-UHFFFAOYSA-N 0.000 claims description 5
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- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 4
- GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 3
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- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
- BMKDZUISNHGIBY-ZETCQYMHSA-N (+)-dexrazoxane Chemical compound C([C@H](C)N1CC(=O)NC(=O)C1)N1CC(=O)NC(=O)C1 BMKDZUISNHGIBY-ZETCQYMHSA-N 0.000 claims description 2
- VVIAGPKUTFNRDU-UHFFFAOYSA-N 6S-folinic acid Natural products C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 VVIAGPKUTFNRDU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72279605P | 2005-09-30 | 2005-09-30 | |
| US60/722,796 | 2005-09-30 | ||
| US83688606P | 2006-08-09 | 2006-08-09 | |
| US60/836,886 | 2006-08-09 | ||
| PCT/US2006/038181 WO2007041362A1 (en) | 2005-09-30 | 2006-09-28 | 2-amino-7,8-dihydro-6h-pyrido[4,3-d] pyrimidin-5-ones |
Publications (2)
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|---|---|
| AU2006297124A1 AU2006297124A1 (en) | 2007-04-12 |
| AU2006297124B2 true AU2006297124B2 (en) | 2011-12-08 |
Family
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|---|---|---|---|
| AU2006297124A Ceased AU2006297124B2 (en) | 2005-09-30 | 2006-09-28 | 2-amino-7,8-dihydro-6H-pyrido(4,3-d) pyrimidin-5-ones |
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| JP (2) | JP5036002B2 (enExample) |
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| AU (1) | AU2006297124B2 (enExample) |
| BR (1) | BRPI0616701A2 (enExample) |
| CA (1) | CA2624253C (enExample) |
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| CY (1) | CY1112028T1 (enExample) |
| DK (1) | DK1928875T3 (enExample) |
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| EC (1) | ECSP088324A (enExample) |
| GE (1) | GEP20115231B (enExample) |
| HR (1) | HRP20110655T1 (enExample) |
| IL (1) | IL190446A0 (enExample) |
| JO (1) | JO2783B1 (enExample) |
| MA (1) | MA29885B1 (enExample) |
| ME (1) | ME01952B (enExample) |
| MY (1) | MY143604A (enExample) |
| NO (1) | NO342258B1 (enExample) |
| NZ (1) | NZ566914A (enExample) |
| PE (1) | PE20070621A1 (enExample) |
| PL (1) | PL1928875T3 (enExample) |
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| RS (1) | RS51795B (enExample) |
| SM (1) | SMP200800029B (enExample) |
| TN (1) | TNSN08143A1 (enExample) |
| TW (1) | TWI373471B (enExample) |
| WO (1) | WO2007041362A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CL2007002994A1 (es) * | 2006-10-19 | 2008-02-08 | Wyeth Corp | Compuestos derivados heterociclicos que contienen sulfamoilo, inhibidores de hsp90; composicion farmaceutica; y uso para el tratamiento del cancer, tal como cancer de mama, de colon y prostata, entre otros. |
| CN101225083A (zh) * | 2007-01-16 | 2008-07-23 | 北京摩力克科技有限公司 | 四氢喹唑啉酮类化合物及其用于制备治疗和预防病毒性疾病的药物的用途 |
| GB2449293A (en) | 2007-05-17 | 2008-11-19 | Evotec | Compounds having Hsp90 inhibitory activity |
| US8071766B2 (en) * | 2008-02-01 | 2011-12-06 | Takeda Pharmaceutical Company Limited | HSP90 inhibitors |
| EP2334379A2 (en) | 2008-09-26 | 2011-06-22 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Host cell kinases as targets for antiviral therapies against hcv infection |
| EP2370103B1 (en) * | 2008-11-28 | 2016-03-23 | Novartis AG | Pharmaceutical combinations comprising an isoxazole derived hsp90-inhibitor and the her2 inhibitor trastuzumab |
| DK2370076T3 (en) * | 2008-11-28 | 2017-04-03 | Novartis Ag | Pharmaceutical combination comprising an Hsp 90 inhibitor and an mTOR inhibitor |
| CN102227220A (zh) * | 2008-11-28 | 2011-10-26 | 诺瓦提斯公司 | 用于治疗性治疗的Hsp90抑制剂 |
| AR075180A1 (es) | 2009-01-29 | 2011-03-16 | Novartis Ag | Formulaciones orales solidas de una pirido-pirimidinona |
| AR077405A1 (es) | 2009-07-10 | 2011-08-24 | Sanofi Aventis | Derivados del indol inhibidores de hsp90, composiciones que los contienen y utilizacion de los mismos para el tratamiento del cancer |
| FR2949467B1 (fr) | 2009-09-03 | 2011-11-25 | Sanofi Aventis | Nouveaux derives de 5,6,7,8-tetrahydroindolizine inhibiteurs d'hsp90, compositions les contenant et utilisation |
| KR101690358B1 (ko) | 2009-10-29 | 2017-01-09 | 제노스코 | 키나아제 억제제 |
| WO2012104823A2 (en) | 2011-02-04 | 2012-08-09 | Novartis Ag | Pyridopyrimidinone compounds in the treatment of neurodegenerative diseases |
| EP2766015A1 (en) | 2011-10-14 | 2014-08-20 | Novartis AG | 2-carboxamide cycloamino urea derivatives in combination with hsp90 inhibitors for the treatment of proliferative diseases |
| ITTO20111013A1 (it) | 2011-11-03 | 2013-05-04 | Dac Srl | Composti farmaceutici |
| CN103664938A (zh) * | 2012-09-12 | 2014-03-26 | 山东亨利医药科技有限责任公司 | 含有嘧啶并环的syk抑制剂 |
| RU2015121424A (ru) | 2012-11-07 | 2016-12-27 | Новартис Аг | Комбинированная терапия |
| US9677907B2 (en) * | 2013-03-14 | 2017-06-13 | Itron Inc | Intelligent receptacle |
| GB201306610D0 (en) * | 2013-04-11 | 2013-05-29 | Almac Discovery Ltd | Pharmaceutical compounds |
| KR101767859B1 (ko) * | 2013-09-30 | 2017-08-11 | 다이호야쿠힌고교 가부시키가이샤 | 아자 2 고리형 화합물을 사용한 암 병용 요법 |
| JP2017525734A (ja) * | 2014-09-02 | 2017-09-07 | ピエール、ファーブル、メディカマン | 癌の治療において有用なイソキノリノン誘導体 |
| KR20160035411A (ko) * | 2014-09-23 | 2016-03-31 | 주식회사 오스코텍 | LRRK2 (Leucine Rich Repeat Kinase 2) 키나제 억제제로서의 피리도피리미딘 유도체 화합물 |
| KR101653560B1 (ko) * | 2016-02-02 | 2016-09-12 | 한국화학연구원 | 신규한 화합물 또는 이의 약학적으로 허용가능한 염, 및 이를 유효성분으로 함유하는 인플루엔자 바이러스 감염으로 인한 질환의 예방 또는 치료용 약학적 조성물 |
| RU2629599C1 (ru) * | 2016-09-28 | 2017-08-30 | Государственное бюджетное учреждение здравоохранения Московской области "Московский областной научно-исследовательский клинический институт им. М.Ф. Владимирского" (ГБУЗ МО МОНИКИ им. М.Ф. Владимирского) | Способ химиолучевого лечения опухолей прямой кишки и анального канала |
| JP7229158B2 (ja) | 2017-06-09 | 2023-02-27 | 中外製薬株式会社 | Ｎ－置換アミノ酸を含むペプチドの合成方法 |
| US20230295108A1 (en) * | 2020-06-26 | 2023-09-21 | Nihon Nohyaku Co., Ltd. | Aryltetrahydropyridine derivative or salt thereof, insecticidal agent containing the compound, and method of use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0278742A2 (en) * | 1987-02-11 | 1988-08-17 | May & Baker Limited | Cyclic diones |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6165873A (ja) * | 1984-09-07 | 1986-04-04 | Mitsui Petrochem Ind Ltd | ２−ピペラジノピリミジン誘導体 |
| CA1307786C (en) | 1984-12-14 | 1992-09-22 | Keiichi Yokoyama | Quinazoline derivatives and antihypertensive preparations containing same as effective components |
| KR100639772B1 (ko) * | 2001-02-12 | 2006-10-30 | 에프. 호프만-라 로슈 아게 | 6-치환된 피리도-피리미딘 |
| DE102004018198A1 (de) | 2004-04-15 | 2005-11-03 | Merck Patent Gmbh | Sulfonamide |
| EP2332527A3 (en) | 2004-10-20 | 2011-11-16 | Resverlogix Corp. | Flavanoids and Isoflavanoids for the prevention and treatment of cardiovascular diseases |
| WO2006074293A2 (en) | 2005-01-07 | 2006-07-13 | President And Fellows Of Harvard College | Bicyclic dihydropyrimidines as eg5 inhibitors |
| US20070027150A1 (en) | 2005-04-14 | 2007-02-01 | Bellamacina Cornelia R | 2-Amino-quinazolin-5-ones |
-
2006
- 2006-09-26 JO JO2006335A patent/JO2783B1/en active
- 2006-09-28 JP JP2008533697A patent/JP5036002B2/ja not_active Expired - Fee Related
- 2006-09-28 HR HR20110655T patent/HRP20110655T1/hr unknown
- 2006-09-28 BR BRPI0616701-2A patent/BRPI0616701A2/pt not_active IP Right Cessation
- 2006-09-28 PT PT06825272T patent/PT1928875E/pt unknown
- 2006-09-28 NZ NZ566914A patent/NZ566914A/en not_active IP Right Cessation
- 2006-09-28 SM SM200800029T patent/SMP200800029B/it unknown
- 2006-09-28 KR KR1020087010134A patent/KR101311757B1/ko not_active Expired - Fee Related
- 2006-09-28 EA EA200800992A patent/EA016152B1/ru not_active IP Right Cessation
- 2006-09-28 ME MEP-2011-334A patent/ME01952B/me unknown
- 2006-09-28 CA CA2624253A patent/CA2624253C/en not_active Expired - Fee Related
- 2006-09-28 EP EP06825272A patent/EP1928875B1/en active Active
- 2006-09-28 GE GEAP200610671A patent/GEP20115231B/en unknown
- 2006-09-28 DK DK06825272.5T patent/DK1928875T3/da active
- 2006-09-28 WO PCT/US2006/038181 patent/WO2007041362A1/en not_active Ceased
- 2006-09-28 AR ARP060104292A patent/AR058072A1/es unknown
- 2006-09-28 US US11/541,462 patent/US7671059B2/en active Active
- 2006-09-28 PL PL06825272T patent/PL1928875T3/pl unknown
- 2006-09-28 RS RS20110334A patent/RS51795B/sr unknown
- 2006-09-28 AU AU2006297124A patent/AU2006297124B2/en not_active Ceased
- 2006-09-28 PE PE2006001177A patent/PE20070621A1/es not_active Application Discontinuation
- 2006-09-28 AT AT06825272T patent/ATE514694T1/de active
- 2006-09-28 MY MYPI20080862A patent/MY143604A/en unknown
- 2006-09-29 TW TW095136162A patent/TWI373471B/zh not_active IP Right Cessation
-
2008
- 2008-03-26 IL IL190446A patent/IL190446A0/en not_active IP Right Cessation
- 2008-03-28 CR CR9846A patent/CR9846A/es unknown
- 2008-03-28 EC EC2008008324A patent/ECSP088324A/es unknown
- 2008-03-28 TN TNP2008000143A patent/TNSN08143A1/en unknown
- 2008-04-24 MA MA30873A patent/MA29885B1/fr unknown
- 2008-04-30 NO NO20082069A patent/NO342258B1/no not_active IP Right Cessation
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2009
- 2009-07-31 US US12/462,302 patent/US20100004237A1/en not_active Abandoned
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2011
- 2011-08-09 CY CY20111100758T patent/CY1112028T1/el unknown
-
2012
- 2012-05-25 JP JP2012119613A patent/JP2012158611A/ja not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0278742A2 (en) * | 1987-02-11 | 1988-08-17 | May & Baker Limited | Cyclic diones |
Non-Patent Citations (1)
| Title |
|---|
| Ashton et al. (1989) Heterocycles 28(2): 1015-1035 * |
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