ES2616477T3 - Heterociclaminas como inhibidores de pi3k - Google Patents
Heterociclaminas como inhibidores de pi3k Download PDFInfo
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- ES2616477T3 ES2616477T3 ES12775861.3T ES12775861T ES2616477T3 ES 2616477 T3 ES2616477 T3 ES 2616477T3 ES 12775861 T ES12775861 T ES 12775861T ES 2616477 T3 ES2616477 T3 ES 2616477T3
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- alkyl
- independently selected
- alkynyl
- alkenyl
- optionally substituted
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- 239000012828 PI3K inhibitor Substances 0.000 title 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 16
- 125000005843 halogen group Chemical group 0.000 abstract 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 9
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 8
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 8
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 6
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 abstract 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 abstract 4
- 125000002947 alkylene group Chemical group 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- -1 -OH Chemical group 0.000 abstract 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000006601 (C1-C3) alkylcarbamyl group Chemical group 0.000 abstract 2
- 102100038417 Cytoplasmic FMR1-interacting protein 1 Human genes 0.000 abstract 2
- 101710181791 Cytoplasmic FMR1-interacting protein 1 Proteins 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 abstract 1
- 125000006599 (C1-C3) alkylaminocarbonylamino group Chemical group 0.000 abstract 1
- 125000006603 (C1-C3) alkylaminosulfonyl group Chemical group 0.000 abstract 1
- 125000006597 (C1-C3) alkylcarbonylamino group Chemical group 0.000 abstract 1
- 125000006595 (C1-C3) alkylsulfinyl group Chemical group 0.000 abstract 1
- 125000006594 (C1-C3) alkylsulfony group Chemical group 0.000 abstract 1
- 125000006602 (C1-C3) alkylsulfonylamino group Chemical group 0.000 abstract 1
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 abstract 1
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 abstract 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 abstract 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 abstract 1
- 125000006593 (C2-C3) alkynyl group Chemical group 0.000 abstract 1
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 abstract 1
- 101100310920 Caenorhabditis elegans sra-2 gene Proteins 0.000 abstract 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical group [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
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
- A61K31/495—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
- 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Un compuesto de Fórmula I: **Fórmula** o una sal farmacéuticamente aceptable del mismo, en donde: X es CR9 o N; W es CR7 o N; Y es CR8, CR8a, o N; Z es un enlace o C(>=O); siempre que -W>=Y-Z- es -CR7>=CR8, -N>=CR8-, -CR7>=CR8a -C(>=O)-, -N>=CR8a -C(>=O)-o -CR7>=NC(>=O)-; R1 es alquilo C1-3; R2 es halo, alquilo C1-6, alcoxi C1-6, haloalquilo C1-6, haloalcoxi C1-6, fenilo o heteroarilo de 5 a 6 miembros; donde dicho fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 sustituyentes seleccionados independientemente de halo, OH, CN, alquilo C1-4, alcoxi C1-4, y haloalcoxi C1-4; R3 es Cy,-(alquileno C1-3)-cy, halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6 ORa, SRa, C(>=O)Rb, C(>=O)NRcRd, C(>=O)ORa, OC(>=O)Rb, OC(>=O)NRcRd, NRcRd, NRcC(>=O)Rb, NRc>=C(>=O)ORb, NRcC(>=O)NRcRd, C(>=NRe)Rb, C(>=NRe) NRcRd, NRcC(>=NRe) NRcRd, NRcS(>=O)2Rb, NRcS(>=O)2NRcRd, S(>=O)2Rb, o S(>=O)2NRcRd; en el que dicho alquilo C1-6, alquenilo C2-6 y alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos independientemente seleccionados 43a; R4 es H, halógeno, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R5 es halo, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, haloalcoxi C1-4, o ciclopropilo; R6 es H, halo, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R7 es H o alquilo C1-4; R7 es H, halo, -OH, -CN, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, Cy2 ,-(alquileno C1-3)-Cy2, ORa2 SRa2, C(>=O)Rb2, C(>=O)NRc2Rd2, C(>=O)ORa2, OC(>=O)Rb2, OC(>=O)NRc2Rd2, NRc2Rd2, NRc2C(>=O)Rb2, NRc2C(>=O)ORb2, NRc2C(>=O)NRc2Rd2, C(>=NRe)Rb2, C(>=NRe) NRc2Rd2, NRc2C(>=NRe) NRc2Rd2, NRc2S(>=O)Rb2, NRc2S(>=O)2NRc2Rd2, S(>=O)Rb2, S(>=O)2Rb2, o S(>=O)2NRc2Rd2; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos seleccionados independientemente R11; R8a es H, halo, -CN, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, Cy2 ,-(alquileno C1-3)-Cy2, C(>=O)Rb2, C(>=O)NRc2Rd2, C(>=O)ORa2, NRc2Rd2, NRc2C(>=O)Rb2, NRc2C(>=O)ORb2, NRc2C(>=O)NRc2Rd2, NRc2S(>=O)Rb2, NRc2S(>=O)2NRc2Rd2, S(>=O)Rb2, S(>=O)2Rb2, o S(>=O)2NRc2Rd2; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2, 3, o 4 grupos seleccionados independientemente R11; R7 es H, halógeno, OH, CN, alquilo C1-4, haloalquilo C1-4, alcoxi C1-4, o haloalcoxi C1-4; R10 es H o alquilo C1-4; cada Ra, Rb, Rc y Rd se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6 y Cy; en el que dicho alquilo C1-6, alquenilo C2-6 y alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R3b seleccionados independientemente; o Rc y Rd junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, o 7 miembros, el cual está opcionalmente sustituido por -OH o alquilo C1-3; cada Re se selecciona independientemente de H, CN, OH, alquilo C1-4, y alcoxi C1-4; cada Cy se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 10 miembros, fenilo, naftilo, y heteroarilo de 5 a 10 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R3b seleccionados independientemente; cada R3a se selecciona independientemente de halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, ORa1, SRa1, C(>=O)Rb1, C(>=O)NRc1Rd1, C(>=O)ORa1, OC(>=O)Rb1, OC(>=O)NRc1Rd1, NRc1Rd1, NRc1C(>=O)Rb1, NRc1C(>=O)ORb1, NRc1C(>=O)NRc1Rd1, C(>=NRe)Rb1, C(>=NRe) NRc1Rd1, NRc1C(>=NRe), NRc1Rd1, NRc1S(>=O)Rb1, NRc1S(>=O)2NRc1Rd1, S(>=O)2Rb1, y S(>=O)2NRc1Rd1; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R11 seleccionados independientemente; cada R3b se selecciona independientemente de Cy1 ,-(alquileno C1-3)-cy1, halo, CN, NO2, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, haloalquilo C1-6, ORa1, SRa1, C(>=O)Rb1, C(>=O)NRc1Rd1, C(>=O)ORa1, OC(>=O)Rb1, OC(>=O)NRc1Rd1, NRc1Rd1, NRc1C(>=O)Rb1, NRc1C(>=O)ORb1, NRc1C(>=O)NRc1Rd1, C(>=NRe)Rb1, C(>=NRe) NRc1Rd1, NRc1C(>=NRe) NRc1Rd1, NRc1S(>=O)Rb1, NRc1S(>=O)2NRc1Rd1, S(>=O)Rb1, S(>=O)2Rb1, y S(>=O)2NRc1Rd1; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6 están cada uno opcionalmente sustituidos por 1, 2 ó 3 grupos R11 seleccionados independientemente; cada Cy1 se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R11 seleccionados independientemente ; cada Ra1, Rb1, Rc1, y Rd1 se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2 o 3 grupos R11 seleccionados independientemente; o Rc1y Rd1 junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, 7 miembros, que está opcionalmente sustituido por -OH o alquilo C1-3; cada Cy2 se selecciona independientemente de cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, heteroarilo de 5 a 6 miembros o heteroarilo bicíclico de 9 a 10 miembros, cada uno de los cuales está opcionalmente sustituido por 1, 2, 3, o 4 grupos R11 seleccionados independientemente; cada Ra2, Rb2, RC2, y Rd2 se selecciona independientemente de H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, alquinilo C2-6, Cicloalquilo C3-7, heterocicloalquilo de 4 a 7 miembros, fenilo, y heteroarilo de 5 a 6 miembros; en el que dicho alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, heterocicloalquilo de 4-7 miembros, fenilo y heteroarilo de 5 a 6 miembros están cada uno opcionalmente sustituidos por 1, 2 o 3 grupos R11 seleccionados independientemente; o Rc2 y Rd2 junto con el átomo N al que están unidos forman un grupo de heterocicloalquilo de 4, 5, 6, o 7 miembros, que está opcionalmente sustituido por -OH o alquilo C1-3; y cada R11 se selecciona independientemente de OH, NO2, CN, halo, alquilo C1-3, alquenilo C2-3, alquinilo C2-3, haloalquilo C1-3, ciano-alquilo C1-3, HO-alquilo C1-3, alcoxi C1-3-alquilo C1-3, cicloalquilo C3-7, alcoxi C1-3, haloalcoxi amino C1-3, alquilamino C1-3, di(alquilo C1-3)amino, tio, alquiltio C1-3, alquilsulfinilo C1-3, alquilsulfonilo C1-3, carbamilo, alquilcarbamilo C1-3, di(alquilo C1-3)carbamilo, carboxi, alquilcarbonilo C1-3, alcoxicarbonilo C1-4, alquilcarbonilamino C1-3, alquilsulfonilamino C1-3, aminosulfonilo, alquilaminosulfonilo C1-3, di(alquilo C1-3)aminosulfonilo, aminosulfonilamino, alquilaminosulfoniloamino C1-3, di(alquilo C1-3)aminosulfonilamino, aminocarbonilamino, alquilaminocarbonilamino C1-3, y di(alquilo C1-3)aminocarbonilamino; en el que los átomos y heteroátomos de un grupo de heterocicloalquilo de carbono que forman anillo pueden estar opcionalmente sustituidos con oxo o sulfido.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161530866P | 2011-09-02 | 2011-09-02 | |
US201161530866P | 2011-09-02 | ||
US201261594882P | 2012-02-03 | 2012-02-03 | |
US201261594882P | 2012-02-03 | ||
US201261677445P | 2012-07-30 | 2012-07-30 | |
US201261677445P | 2012-07-30 | ||
PCT/US2012/053398 WO2013033569A1 (en) | 2011-09-02 | 2012-08-31 | Heterocyclylamines as pi3k inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2616477T3 true ES2616477T3 (es) | 2017-06-13 |
Family
ID=47071429
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES18215449T Active ES2873001T3 (es) | 2011-09-02 | 2012-08-31 | Heterociclaminas como inhibidores de PI3K |
ES16199883T Active ES2722524T3 (es) | 2011-09-02 | 2012-08-31 | Heterociclaminas como inhibidores de pi3k |
ES12775861.3T Active ES2616477T3 (es) | 2011-09-02 | 2012-08-31 | Heterociclaminas como inhibidores de pi3k |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES18215449T Active ES2873001T3 (es) | 2011-09-02 | 2012-08-31 | Heterociclaminas como inhibidores de PI3K |
ES16199883T Active ES2722524T3 (es) | 2011-09-02 | 2012-08-31 | Heterociclaminas como inhibidores de pi3k |
Country Status (38)
Country | Link |
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US (9) | US9199982B2 (es) |
EP (4) | EP2751109B1 (es) |
JP (8) | JP6067709B2 (es) |
KR (7) | KR101982475B1 (es) |
CN (1) | CN106986867B (es) |
AR (1) | AR087760A1 (es) |
AU (5) | AU2012301721B2 (es) |
BR (2) | BR122019020716B1 (es) |
CA (1) | CA2846652C (es) |
CL (1) | CL2014000517A1 (es) |
CO (1) | CO6910199A2 (es) |
CR (2) | CR20180293A (es) |
CY (3) | CY1118679T1 (es) |
DK (3) | DK3513793T3 (es) |
EA (2) | EA028890B1 (es) |
EC (1) | ECSP14013274A (es) |
ES (3) | ES2873001T3 (es) |
HK (1) | HK1199644A1 (es) |
HR (3) | HRP20170285T1 (es) |
HU (3) | HUE030869T2 (es) |
IL (7) | IL314671A (es) |
LT (3) | LT3513793T (es) |
ME (2) | ME03397B (es) |
MX (2) | MX2020004502A (es) |
MY (1) | MY179332A (es) |
NZ (1) | NZ769326A (es) |
PE (2) | PE20181272A1 (es) |
PH (2) | PH12017501766B1 (es) |
PL (3) | PL2751109T3 (es) |
PT (3) | PT2751109T (es) |
RS (3) | RS61761B1 (es) |
SG (3) | SG10201912484RA (es) |
SI (3) | SI2751109T1 (es) |
SM (1) | SMT201700111B (es) |
TW (6) | TWI648277B (es) |
UA (1) | UA121539C2 (es) |
WO (1) | WO2013033569A1 (es) |
ZA (1) | ZA201904877B (es) |
Families Citing this family (55)
Publication number | Priority date | Publication date | Assignee | Title |
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TW201602113A (zh) * | 2009-06-29 | 2016-01-16 | 英塞特公司 | 作為pi3k抑制劑之嘧啶酮 |
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