AR091236A1 - Compuestos de tetrahidropirazolopirimidina - Google Patents
Compuestos de tetrahidropirazolopirimidinaInfo
- Publication number
- AR091236A1 AR091236A1 ARP130101930A AR091236A1 AR 091236 A1 AR091236 A1 AR 091236A1 AR P130101930 A ARP130101930 A AR P130101930A AR 091236 A1 AR091236 A1 AR 091236A1
- Authority
- AR
- Argentina
- Prior art keywords
- optionally substituted
- formula
- och3
- nitrogen
- atoms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 24
- -1 1,4-dimethylthiazolyl Chemical group 0.000 abstract 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 16
- 229910052757 nitrogen Inorganic materials 0.000 abstract 14
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- 125000004193 piperazinyl group Chemical group 0.000 abstract 6
- 125000003386 piperidinyl group Chemical group 0.000 abstract 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 150000001555 benzenes Chemical class 0.000 abstract 3
- 229910052799 carbon Inorganic materials 0.000 abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 3
- 150000003222 pyridines Chemical class 0.000 abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 3
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 125000002393 azetidinyl group Chemical group 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 abstract 1
- 150000002460 imidazoles Chemical class 0.000 abstract 1
- 150000002461 imidazolidines Chemical class 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 150000003854 isothiazoles Chemical class 0.000 abstract 1
- 125000006384 methylpyridyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003218 pyrazolidines Chemical class 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003233 pyrroles Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
Classifications
-
- 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
-
- 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
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- 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
- A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
- 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
- C07D487/10—Spiro-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
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (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)
- Plural Heterocyclic Compounds (AREA)
Abstract
Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1) o una sal farmacéuticamente aceptable del mismo, o un estereoisómero del mismo o mezcla de estereoisómeros del mismo, donde R¹ es piperidinilo opcionalmente sustituido, piridilo opcionalmente sustituido, pirrolilo opcionalmente sustituido, pirroldinilo opcionalmente sustituido, 1,4-dimetiltiazolilo, 2-etil-4-metiltiazolilo, 2-isopropiltiazol-5-ilo, tiazolilo, 3-etiltiazol-5-ilo, 1-metilsulfonilpiperidin-4-ilo, o R¹ es -C(O)Z, donde Z es piperazinilo, (S)-2-(3-etilpiperazin-1-ilo), pirrolopirrolilo opcionalmente sustituido, piperidin-3-ilamino, o, R¹ es un resto de fórmula (2), donde R¹³ es H, metilpirazolilo, metilimidazolilo, bencilo, 3-hidroxibutilo, 3-(dimetilamino)-2,2-dimetilpropilo, etilamida, metilpiridilo, metilsulfonilo, (1-metilimidazol-2-il)metilo, (1,5-dimetilimidazol-4-il)metilo, (1-metilpirrol-2-il)metilo, o donde R¹³ es C(O)W, donde W es -N(CH₃)₂, piperidinilo, piperazinilo, o morfolinilo, o, R¹ es un resto de fórmula (3), donde R¹⁴ es -C(O)CH₃, H, o (1-metilpirrol-2-il)metilo, o, R¹ es un resto seleccionado del grupo de fórmulas (4), o R¹ es un compuesto de fórmula (5) donde A, B, y D pueden ser todos carbonos, o donde dos de A, B, y D son carbono y el otro es nitrógeno, o donde uno de A, B, y D es carbono y los restantes dos son nitrógeno; y cuando A es nitrógeno R⁴ se encuentra ausente, cuando B es nitrógeno R² se encuentra ausente y cuando D es nitrógeno R³ se encuentra ausente; y donde R² es H, -CH₃, o F, o, con R³ y los átomos en las posiciones a y b, forma una piridina opcionalmente sustituida o un pirazol; y donde R³ es H, F, Cl, -CN, -CH₃, -OCH₃, -OH, -NH₂, metilsulfonilo, o un resto del grupo de fórmulas (6), o, con R⁴ y los átomos en las posiciones b y c, forma un benceno opcionalmente sustituido, imidazol opcionalmente sustituido, pirazol opcionalmente sustituido, pirazolidina opcionalmente sustituida, imidazolidina opcionalmente sustituida, isotiazol opcionalmente sustituido, un resto de fórmula (7) o, con R² y los átomos en las posiciones a y b, forma una piridina opcionalmente sustituida o pirazol opcionalmente sustituido; y donde R⁴ es F, -CN, -OCH₃, -OEt, H, Cl, Br, -NH-C(O)-CH-(CH₃)₂, -N(CH₃)₂, -CH₃, -CH₂OH, un resto de fórmula (8), (9) ó (10), piperazinilo opcionalmente sustituido, 4-hidroxipiperizin-1-ilo, piperidinilo opcionalmente sustituido no unido a un grupo fenilo a través de un nitrógeno, o, con R³ y los átomos en las posiciones b y c, forma un anillo pirazol opcionalmente sustituido o el resto de fórmula (7), o, con R⁵ y los átomos en las posiciones c y d, forma un anillo pirazol opcionalmente sustituido o un anillo pirrol opcionalmente sustituido, o, R⁴ es -(q)-C(O)X, donde q es una unión, es -NH-, o es -CH₂-, y donde X es -NR¹¹R¹², donde R¹¹ y R¹² son ambos H, ambos -CH₂CH₃, o ambos -CH₃, o donde uno de R¹¹ y R¹² es H y el otro es 1,1-dimetiletilo, ciclobutilo, ciclopropilo, alquilo inferior, alcohol metílico, alcohol propílico, ciclobutilmetilo; 2,3-dihidroxipropilo, bencilo, azetidinilo, pirrolidinilo, piperidinilo, metilazetidinilo, -CH₂-NH-CH₃, pirazolilo, piperazinilo, alcohol, -OCH₃, o un resto de fórmula (11), o donde X es pirrolidinilo opcionalmente sustituido unido a través de un nitrógeno al grupo carbonilo de R⁴, piperidinilo opcionalmente sustituido no unido a través de un nitrógeno al grupo carbonilo de R⁴, pirrolidinilo opcionalmente sustituido unido a través de un nitrógeno al grupo carbonilo de R⁴, piperazinilo opcionalmente sustituido unido a través de un nitrógeno al grupo carbonilo de R⁴, o morfolinilo opcionalmente sustituido unido a través de un nitrógeno al grupo carbonilo de R⁴, o un compuesto seleccionado del grupo de fórmulas (12); y donde R⁵ es H, F, Cl, -CH₃, -OCH₃, pirrolilo, -CH₂OH, -NH₂, -OH, un resto de fórmula (13), o de fórmula (14), o, con R⁴ y los átomos en las posiciones c y d, forma un benceno opcionalmente sustituido, un pirazol opcionalmente sustituido, o un pirrol opcionalmente sustituido, o, con R⁶ y los átomos en las posiciones d y e, forma una piridina opcionalmente sustituida, o R⁵ es C(O)Y, donde Y es -NH₂, -N(CH₃)₂, piperazinilo opcionalmente sustituido, piperidinilo opcionalmente sustituido, o un resto del grupo de fórmulas (15); y donde R⁶ es H, F, -CH₃, -CF₃, o, con R⁵ y los átomos en las posiciones c y d, forma un benceno opcionalmente sustituido o un pirazol opcionalmente sustituido; y donde R⁷ es -CF₃ o -CHF₂; y donde R⁸ es un resto de fórmula (16) ó (17); y donde R⁹ es Br, Cl, F, l, o H; con las siguientes condiciones: cuando R⁴ es F: R² no es -CH₃ o F; R³ no es -CH₃, -CN, F, Cl, o -OCH₃; R⁵ no es -CH₃, F, Cl, o -OCH₃; y R⁶ no es -CH₃ o F; cuando R⁴ es Cl: R² no es F; R³ no es F o -CN; R⁵ no es F, -CN, o -C(O)N(CH₃)₂; R⁶ no es -CF₃ o F; D no es nitrógeno; y o bien R⁵ es -C(O)NH₂ o uno de R², R³, R⁵, y R⁶ es -CH₃; cuando R⁴ es -CH₃: R³ no es F; R⁵ no es F; y R⁵ y R⁶ no forman una pirimidina junto con los átomos en las posiciones d y e; cuando R⁴ es -OCH₃: R² no es F; R³ no es Cl o -OCH₃, R⁵ no es Cl o -OCH₃; y R⁶ no es F o -CF₃; cuando R⁴ es -CN: R² no es F; R³ no es Cl, F, o -OCH₃, R⁵ no es Cl, F, o -OCH₃; y R⁶ no es F; cuando R⁴ es -OCH₂CH₃: R³ no es Cl o F; R⁵ no es Cl o F; y R⁶ no es -CF₃; cuando R⁴ es un resto de fórmula (18): R³ no es H o F; y R⁵ no es H o F; cuando R⁴ es el resto de fórmula (18): al menos uno de R², R³, R⁵, y R⁶ no es H; cuando R⁴ es un compuesto de fórmula (19): R³ no es F; y R⁵ no es F; cuando R² es F: R³ no es -OCH₃ o F; R⁵ no es -CN; y al menos uno de R³, R⁴, R⁵, y R⁶ no es H; cuando R² es Cl: R³ no es F; cuando R² es -CH₃: R³ no es Cl; al menos uno de R³, R⁴, R⁵, y R⁶ no es -CH₃; y R⁴ y R⁵ no forman un pirazolilo con los átomos en las posiciones c y d; cuando R³ es -OCH₃: R² no es F; y R⁶ no es F; cuando R³ es F: R² no es -OCH₃; y X no es un resto de fórmula (20); cuando R³ es Cl; R⁵ no es Cl; R¹¹, no es bencilo; y R¹² no es bencilo; cuando R⁵ es Cl, R⁶ no es -CH₃; R¹¹ no es bencilo; y R¹² no es bencilo; cuando R⁵ es F o -OCH₃: R⁶ no es F; cuando R⁶ es F: al menos uno de R², R³, R⁴, y R⁵ no es H; cuando R³ y R⁵ son H: R¹¹ no es ciclopropilo; y R¹² no es ciclopropilo; cuando R⁹ es Cl, R¹ no es un grupo amida; cuando B es nitrógeno y A y D son carbono: R⁴ no puede ser -CN o el resto de fórmula (21); cuando R⁷ es -CHF₂ y R⁴ es un resto de fórmula (22), luego R⁴ no tiene la estereoquímica absoluta de fórmula (23); y donde, cuando R⁸ es el compuesto de fórmula (17) entonces se aplican las siguientes condiciones: cuando R⁴ es F; al menos uno de R², R³, R⁵, y R⁶ no es H; R³ no es C(O)N(CH₃)₂; y R⁵ no es C(O)N(CH₃)₂; cuando R⁴ es Cl: al menos uno de R², R³, R⁵, y R⁶ no es H; cuando R³ es F: R⁴ no es C(O)NHCH₂CH₂CH₂CH₃, C(O)N(CH₃)₂, C(O)NHCH₂CH₂CH₃, o C(O)NHC(CH₃)₃; R⁴ no es C(O)NHCH₂CH₂CH₂OH, C(O)NHCH(CH₃)₂, -CN, o el resto de fórmula (24); R¹ no es un compuesto de fórmula (25) ó (26); R⁵ no es el resto de fórmula (27); R³ no es el resto de fórmula (28); cuando R² es F: R⁵ no es -C(O)NH₂; cuando R² es -CH₃, R⁴ y R⁵ no forman un pirazol con los átomos en las posiciones c y d; y cuando B es nitrógeno, R³ y R⁴ no forman un imidazol opcionalmente sustituido con los átomos en las posiciones b y c; y donde, cuando R⁸ es el compuesto de fórmula (29), entonces se aplican las siguientes condiciones: R⁴ no es -CH₃, -C(O)NHCH₂CH₂OH, -NHC(O)CH(CH₃)₂, o un resto de fórmula (30); cuando R⁴ es C(O)NHCH₃, al menos uno de R², R³, R⁵, y R⁶ no es H; cuando R⁴ es -OCH₃: R³ no es F o -CH₃ y R⁵ no es F o -CH₃; cuando R⁴ es el compuesto de fórmula (31): R³ no es Cl; y R⁵ no es Cl; cuando R⁴ es -C(O)NHCH(CH₃)₂ o -C(O)N(CH₂CH₃)₂: al menos uno de R³ y R⁵ no es H; R⁵ no es -C(O)NH₂; y R⁶ no es -CF₃.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261654023P | 2012-05-31 | 2012-05-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR091236A1 true AR091236A1 (es) | 2015-01-21 |
Family
ID=48626649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130101930 AR091236A1 (es) | 2012-05-31 | 2013-05-31 | Compuestos de tetrahidropirazolopirimidina |
Country Status (34)
| Country | Link |
|---|---|
| US (5) | US9126999B2 (es) |
| EP (1) | EP2855476B1 (es) |
| JP (2) | JP6285918B2 (es) |
| KR (2) | KR102268155B1 (es) |
| CN (2) | CN104507939B (es) |
| AR (1) | AR091236A1 (es) |
| AU (2) | AU2013267204B8 (es) |
| BR (1) | BR112014030060B1 (es) |
| CA (1) | CA2874445C (es) |
| CL (1) | CL2014003278A1 (es) |
| CY (1) | CY1122692T1 (es) |
| DK (1) | DK2855476T3 (es) |
| ES (1) | ES2709119T3 (es) |
| HK (1) | HK1203498A1 (es) |
| HR (1) | HRP20181889T1 (es) |
| HU (1) | HUE040562T2 (es) |
| IL (2) | IL268013B2 (es) |
| JO (1) | JO3407B1 (es) |
| LT (1) | LT2855476T (es) |
| MX (1) | MX368455B (es) |
| MY (1) | MY172926A (es) |
| NZ (1) | NZ703459A (es) |
| PE (2) | PE20150220A1 (es) |
| PH (2) | PH12014502660B1 (es) |
| PL (1) | PL2855476T3 (es) |
| PT (1) | PT2855476T (es) |
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