CO4980857A1 - Piridinas biciclicas, intermediarios de ellas, proceso para su preparacion y preparaciones farmaceuticas que contienen las mismas. - Google Patents
Piridinas biciclicas, intermediarios de ellas, proceso para su preparacion y preparaciones farmaceuticas que contienen las mismas.Info
- Publication number
- CO4980857A1 CO4980857A1 CO98060325A CO98060325A CO4980857A1 CO 4980857 A1 CO4980857 A1 CO 4980857A1 CO 98060325 A CO98060325 A CO 98060325A CO 98060325 A CO98060325 A CO 98060325A CO 4980857 A1 CO4980857 A1 CO 4980857A1
- Authority
- CO
- Colombia
- Prior art keywords
- alkyl
- hydrogen
- amino
- heteroalkyl
- heterocyclylalkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title 1
- 239000000825 pharmaceutical preparation Substances 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 38
- 229910052739 hydrogen Inorganic materials 0.000 abstract 27
- 239000001257 hydrogen Substances 0.000 abstract 27
- 125000004404 heteroalkyl group Chemical group 0.000 abstract 17
- 150000002431 hydrogen Chemical group 0.000 abstract 14
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 12
- 125000002947 alkylene group Chemical group 0.000 abstract 10
- 125000000623 heterocyclic group Chemical group 0.000 abstract 9
- -1 nitro, cyano, amino, monosubstituted amino Chemical group 0.000 abstract 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 6
- 125000001188 haloalkyl group Chemical group 0.000 abstract 6
- 125000004475 heteroaralkyl group Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 5
- 125000004442 acylamino group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000304 alkynyl group Chemical group 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 abstract 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 2
- 125000006413 ring segment Chemical group 0.000 abstract 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 abstract 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
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- 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]
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/18—Oxygen or sulfur atoms
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- 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
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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Abstract
Un compuesto seleccionado del grupo de compuestos representadospor la fórmula(I): en los que: R1 es heteroarilo; ------representa un enlace entre o bien B y CR1 o Q y CR1 de modo que: (i) cuando------ es entre Q y -CR1 -entonces: B es nitrógeno; R2 es arilo; y Q es -CR- donde: R es hidrógeno, alquilo, haloalquilo, cicloalquilo, R2 es arilo; y Q es -CR-donde:R es hidrógeno, alquilo, haloalquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo, acilo, heterociclilo, heterociclilalquilo, heterociclilcarbonilo, nitro, ciano, amino, amino monosubstituido, amino disubstituido, acilamino, sulfonilamino, -OR5 (donde R5 es hidrógeno, alquilo, heteroalquilo, o heterociclilalquilo), -COOR7 (donde R7 es hidrógeno o alquilo) o -CONR´R" (donde R´y R" independientemente representan hidrógeno, alquilo o heteroalquilo); y (ii) cuando ------ es entre B y -CR1 -entonces: B es carbono; R2 es arilo o heteroarilo; y Q es -NR4 -, -O-, o -S-donde: R4 es hidrógeno, alquilo, alquenilo, alquinilo, haloalquilo, cicloalquilo, cicloalquilalquilo, heteroalquilo, acilo, aralquilo, heteroaralquilo, heterociclilo, heterociclilalquilo, heterociclilcarbonilo, -OR5 (donde R5 es hidrógeno, alquilo, heteroalquilo, o heterociclilalquilo), - 2 --SO2 R" (donde R" es alquilo, amino, amino monosubstituido o amino disubstituido), -CONR´R" (donde R´y R" independientemente representan hidrógeno, alquilo, o heteroalquilo), -(alquileno)-Z o -(alquileno)-CO-(alquileno) -Z donde: Z es ciano; -COOR7 donde R7 es hidrógeno o alquilo; -CONR8 R9 donde R8 es hidrógeno o alquilo, R9 es alcoxi o -(alquileno)-COOR7 , o R8 y R9 junto con el átomo de nitrógeno con el que están unidos forman un heterociclo; -C(=NR10 )(NR11 R12 )donde R10 , R11 y R12 independientemente representan hidrógeno o alquilo, o R10 y R11 juntos son -(CH2 )n -donde n es 2 ó 3 y R12 es hidrógeno o alquilo; o -COR13 donde R13 es alquilo, heteroalquilo, heterociclilalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo, y es un grupo representado por la fórmula (S), (T), (U), (V) o (W); donde: R6 es hidrógeno, alquilo, heteroalquilo, heterociclilalquilo, halo, ciano, nitro, amino, amino monosubstituido, amino disubstituido, -COOR14 , -(alquileno)-COOR14 (donde R14 es hidrógeno o alquilo), -CONR15 R16 (donde R15 y R16 independientemente representan hidrógeno o alquilo, o R15 y R16 junto con el átomo de nitrógeno con el que están unidos forman un heterociclo), -S(O)n R17 (donde n es un entero de O a 2 y R17 es alquilo, amino, amino monosubstituido o amino disubstituido), -OR18 (donde R18 es hidrógeno, alquilo, heteroalquilo o heterociclialquilo), -NRC(O)R" [donde R es hidrógeno, alquilo o hidroxialquilo y R" es hidrógeno, alquilo, cicloalquilo, o -(alquileno)-X donde X es hidroxi, alcoxi, amino, alquilamino, dialquilamino, heterociclilo o -S(O)n R´ (donde n es de 0 a 2 y R´ es alquilo)], -NRSO2 R" [donde R es hidrógeno o alquilo y R´´ es alquilo o -(alquileno)-X donde X es hidroxi, alcoxi, amino, alquilamino, dialquilamino o -S(O)n R´ (donde n es de 0 a 2 y R´ es alquilo)]; y R3 es hidrógeno, alquilo, alquenilo, alquinilo, haloalquilo, heteroalquilo, cicloalquilo, cicloalquilalaquilo, cicloalquiltio, aralquilo, heteroaralquilo, heterociclilo, heterociclilalquilo, halo, ciano, nitro, amino, amino monosubstituido, amino disubstituido, acilamino, sulfonilamino, -OR19 (donde R19 es hidrógeno, alquilo, heteroalquilo, o heterociclilalquilo), -COOR20 (donde R20 es hidrógeno o alquilo), -CONR21 R22 (donde R21 y R22 independientemente representa hidrógeno, alquilo o heteroalquilo, o R21 y R22 juntos con el átomo de nitrógeno con el que están unidos forman un heterociclo, -S(O)n R23 (donde n es un entero de 0 a 2 y R23 es alquilo, heteroalquilo, amino, amino monosustituido o amino disubstituido), -(alquileno)-Z" o -(alquileno)-CO-(alquileno)-Z" donde: Z" es ciano; -COOR24 donde R24 es hidrógeno o alquilo; -CONR25 R26 donde R25 R26 independientemente representan hidrógeno o alquilo, o R25 y R26 juntos con el átomo de nitrógeno con el que están unidos forman un heterociclo; -C(=NR27 ) (NR28 R29 ) donde R27 , R28 y R29 independientemente representan hidrógeno o alquilo, o R27 y R28 juntos son -(CH2 )n donde n es 2 o 3 y R29 es hidrógeno o alquilo; o -COR30 donde R30 es alquilo, heteroalquilo, heterociclialquilo, arilo, aralquilo, heteroarilo, o heteroaralquilo; en donde el alquilo tiene de 1 a 6 átomos de carbono, el alquenilo tiene de 2 a 6 átomos de carbono, el alquinilo tiene de 3 a 6 átomos de carbono, el cicloalquilo tiene de 3 a 6 átomos de carbono, el heteroalquilo tiene de 1 a 6 átomos de carbono, el heterociclilo tiene un anillo de 3 a 8 átomos de carbono en el cual uno o dos átomos del anillo son heteroátomos seleccionados de N; O o S(O)n (en donde n es un entero de 0 a 2), los restantes átomos del anillo son carbonos en donde uno o dos átomos de carbono pueden opcionalmente ser reemplazados por un grupo carbonilo; amino monosustituido significa un radical -NHR en donde R es alquilo, alquenilo, heteroalquilo, haloalquilo, heterociclilalquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, heteroarilo, heteroaralquilo o un grupo protector de amino y amino disubstituido significa un radical -NRR en el que R y R´ son independientemente alquilo, alquenilo, heteroalquilo, haloalquilo, heterociclilalquilo, cicloalquilo, cicloalquilalquilo, arilo, aralquilo, heteroarilo o heteroaralquilo; y sus sales profármacos, isómeros individuales y mezclas de isómeros farmacéuticamente aceptables, con la condición de que ambos R3 y R6 no son amino, amino monosubstituido o amino disubstituido.
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US6254897P | 1997-10-20 | 1997-10-20 | |
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CO98060325A CO4980857A1 (es) | 1997-10-20 | 1998-10-16 | Piridinas biciclicas, intermediarios de ellas, proceso para su preparacion y preparaciones farmaceuticas que contienen las mismas. |
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FR2732969B1 (fr) | 1995-04-14 | 1997-05-16 | Adir | Nouveaux composes pyridiniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
EP0871444A4 (en) * | 1995-08-10 | 1999-01-13 | Merck & Co Inc | 2.5 SUBSTITUTED ARYL PYRROL, THE COMPOSITIONS THAT CONTAIN AND THE USE THEREOF |
WO1997049706A1 (en) | 1996-06-25 | 1997-12-31 | Novartis Ag | SUBSTITUTED 7-AMINO-PYRROLO[3,2-d]PYRIMIDINES AND THE USE THEREOF |
PT948495E (pt) * | 1996-11-19 | 2004-08-31 | Amgen Inc | Agentes anti-inflamatorios de pirrolo fundido substituidos em arilo e heteroarilo |
WO1998047899A1 (en) | 1997-04-24 | 1998-10-29 | Ortho-Mcneil Corporation, Inc. | Substituted pyrrolopyridines useful in the treatment of inflammatory diseases |
-
1998
- 1998-10-13 AU AU97499/98A patent/AU745579B2/en not_active Ceased
- 1998-10-13 HU HU0100348A patent/HUP0100348A3/hu unknown
- 1998-10-13 EP EP98951516A patent/EP1025102B1/en not_active Expired - Lifetime
- 1998-10-13 KR KR10-2000-7004272A patent/KR100378937B1/ko not_active IP Right Cessation
- 1998-10-13 ID IDW20000729A patent/ID27124A/id unknown
- 1998-10-13 NZ NZ503685A patent/NZ503685A/en unknown
- 1998-10-13 ES ES98951516T patent/ES2221213T3/es not_active Expired - Lifetime
- 1998-10-13 YU YU22000A patent/YU22000A/sh unknown
- 1998-10-13 CA CA002306870A patent/CA2306870A1/en not_active Abandoned
- 1998-10-13 CN CN98811246A patent/CN1279682A/zh active Pending
- 1998-10-13 PL PL98340412A patent/PL340412A1/xx unknown
- 1998-10-13 BR BR9812944-9A patent/BR9812944A/pt not_active IP Right Cessation
- 1998-10-13 WO PCT/EP1998/006472 patent/WO1999020624A1/en active IP Right Grant
- 1998-10-13 TR TR2000/01079T patent/TR200001079T2/xx unknown
- 1998-10-13 DE DE69824029T patent/DE69824029T2/de not_active Expired - Fee Related
- 1998-10-13 IL IL13530298A patent/IL135302A0/xx unknown
- 1998-10-13 AT AT98951516T patent/ATE267200T1/de not_active IP Right Cessation
- 1998-10-13 JP JP2000516966A patent/JP3579350B2/ja not_active Expired - Fee Related
- 1998-10-13 RU RU2000110738/04A patent/RU2219178C2/ru not_active IP Right Cessation
- 1998-10-16 US US09/174,299 patent/US6316464B1/en not_active Expired - Fee Related
- 1998-10-16 MA MA25301A patent/MA26555A1/fr unknown
- 1998-10-16 PE PE1998000976A patent/PE120999A1/es not_active Application Discontinuation
- 1998-10-16 CO CO98060325A patent/CO4980857A1/es unknown
- 1998-10-19 TW TW087117244A patent/TWI224596B/zh not_active IP Right Cessation
-
2000
- 2000-04-12 HR HR20000209A patent/HRP20000209A2/hr not_active Application Discontinuation
- 2000-04-13 NO NO20001940A patent/NO316734B1/no not_active IP Right Cessation
-
2001
- 2001-04-19 US US09/839,710 patent/US6630485B2/en not_active Expired - Fee Related
- 2001-04-19 US US09/839,712 patent/US6479507B2/en not_active Expired - Fee Related
-
2002
- 2002-09-17 US US10/245,906 patent/US20030139462A1/en not_active Abandoned
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