Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Reexamination Certificate
2003-12-18
2009-11-03
Bernhardt, Emily (Department: 1624)
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
C544S060000, C544S140000, C544S364000, C544S367000, C544S370000, C544S371000, C546S210000
Reexamination Certificate
active
07612201
ABSTRACT:
Compounds of formula (IA) or (IB) or a salt, N-oxide, hydrate or solvate thereof are inhibitors of HSP90, and are of value in the treatment of diseases responsive to HSP90 inhibition such as cancers. In the formulae, Ar is an aryl, aryl(C1-C6alkyl), aryl(C1-C6alkyl), heteroaryl, heteroarylaryl(C1-C6alkyl), or heteroarylaryl(C1-C6alkyl) group, any of which being optionally substituted in the aryl or heteroaryl part thereof; R1, is hydrogen or optionally substituted C1-C6alkyl; R2is hydrogen, optionally substituted cycloalkyl, cycloalkenyl, C1-C6alkyl, C1-C6alkenyl, or C1-C6alkynyl; or a carboxyl, carboxamide or carboxyl ester group; and ring A is a non aromatic carbocyclic or heterocyclic ring wherein (i) a ring carbon is optionally substituted, and/or (ii) a ring nitrogen is optionally substituted by a group of formula -(Alk1)p(Cyc)n-(Alk3)m-(Z)r (Alk2)sQ where Alk1, Alk2and Alk3are optionally substituted C1-C3alkyl, Cyc is an optionally substituted carbocyclic or heterocyclic radical; m, n, p, r and s are independently 0 or 1, Z is -0-, —S—, —(C═O)—, —S02-, —C(═O)O—, —OC(═O)—, —NW—, —C(═O)NRA-, —NRAC(═O)—, —SO2NRA—, or —NRASO2— wherein RAis hydrogen or C1-C6alkyl, and Q is hydrogen or an optionally substituted carbocyclic or heterocyclic radical.
REFERENCES:
patent: 5486534 (1996-01-01), Lee et al.
patent: 10307329 (2004-08-01), None
patent: 63 253068 (1988-10-01), None
patent: 96 03385 (1996-02-01), None
patent: WO 97 01551 (1997-01-01), None
patent: WO 98 52940 (1998-11-01), None
patent: WO 00 31063 (2000-06-01), None
patent: WO 01 79187 (2001-10-01), None
patent: WO 03 055860 (2003-07-01), None
patent: WO 03 062206 (2003-07-01), None
Vippagunta et al. Advanced Drug Delivery Reviews, vol. 48, p. 3-26 (2001).
Barril et al. Bioorganic & Medicinal Chemistry Letters, vol. 16, pp. 2543-2548 (2006).
Dymock et al. Expert Opin.Ther.Patents, vol. 14(6), pp. 837-847 (2004). Available online at http://www.expertopin.com/doi/pdf/10.1517/13543776.14.6.837.
Database Chemcats 'Online! American Chemical Society; retrieved from STN, XP002275488, RNs 512817-94-6, dated May 19, 2003; 512812-41-8, dated May 19, 2003; 512817-19-5, dated May 19, 2003; 512817-26-4, dated May 19, 2003; 494867-78-6, dated Apr. 29, 2003.
Database Chemcats 'Online! American Chemical Society; retrieved from STN, XP002275489 RNs 494867-81-1, dated Jul. 9, 2002; 442643-27-8, dated Jul. 9, 2002; 442642-90-2, dated Jul. 9, 2002; 430450-02-5, dated Jan. 17, 2002; 442643-55-2, dated Jan. 17, 2002; 426252-69-9, dated Jul. 9, 2002; 426246-04-7, dated Jul. 9, 2002; 428478-82-4, dated Jul. 9, 2002, 2002; 426242-81-1, dated Jul. 9, 2002; 426241-82-9, dated Jul. 9, 2002; 428480-97-1, dated Jan. 17, 2002; 428479-84-9 dated Jan. 17, 2002.
Patent Abstracts of Japan vol. 013, No. 061 (C-567), Feb. 10, 1989.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Sausins, A, et al: “Methods of synthesis of 4-(pyrazolyl)- and 4-(pyridy1)-5-oxo-1,4,5,7-tetrahydrofuro'3,4- b!pyridines” retrieved from STN, Database accession no. 124:202067 XP002275490, RNs 154926-86-0, 174314-90-0, 174314-91-1,174314-93-3, 174314-96-6, 174314-97-7, 174314-98-8 & Khimiya Geterotsiklicheskikh Soedinenii (1995), (7), 966-72.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Baraldi, P.G. et al: 'Synthesis and cardiodepressant activity of dialkyl 1, 4-dihydro-2, 6-dimethy1-4-(pentatomic-heteroaryl)-3,5-pyridinedicarboxylates. 2 retrieved from STN, Database accession No. 120:289435, XP002275491 abstract; RN 154926-86-0 & Drug Design and Discovery (1993), 10(4), 319-29.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Shanker, M.S.S. et al: “A novel synthesis of pyrazolylchromone derivatives” retrieved from STN, Database accession No. 116:128767 XP002275492 RN 139394-43-7 & Asian Journal of Chemistry (1992), 4(1), 166-70.
Database CA 'Online! Chemical Abstracts Service; Columbus, Ohio, US; Cekavicius, B et al: “Synthesis and hepatoprotective properties of 4-pyrazolyl-1, 4-dihydropyridines” retrieved from STN, Database accession No. 108:68683, XP002275493 abstract; RN 112758-37-9 & Khimiko-Farmatsevticheskii Zhurnal (1987), 21(8), 959-65,.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Hoffmann, Michael G. et al: “O-Glycosylimidates. 19. Reaction of glycosyltrichloroacetimidates with silylated C-nucleophiles” retrieved from STN, Database accession No. 104:51038, XP002275494 RNs 99701-82-3, 99701-81-2, 99701-83-4 & Liebigs Annalen Der Chemie (1985), (12), 2403-19.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Alonso, G. et al: “Synthesis of pyrazole C-nucleosides by 1,3-dipolar cycloaddition” retrieved from STN Database accession No. 87:184819, XP002275495 RN 64559-22-4 & Anales De Quinica (1968-1979) (1976), 72(11-12), 987-90.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Arakawa, Kiichi. et al: “Synthesis of 1-(3-phenylpyrazol-4-yl) beta.-D-ribofuranoside, a C-nucleoside” retrieved from STN, Database accession No. 82:73382, XP002275496 RNs 54680-27-2, 54680-28-3, 54680-29-4, 54680-30-7& Chemistry Letters (1974), (11), 1305-8.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Garcia-Lopez, M. T.. et al: “Synthesis of heterocyclic C-glycosyl compounds by 1,3-dipolar cycloaddition of diazomethane to acetylenic-carbohydrate derivatives” retrieved from STN, Database accession No. 75:88530, XP002275497 RNs 34020-52-5, 34020-53-6 & Journal of Heterocyclic Chemistry (1971), 8(3), 525.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Terent'EV, P.B.. et al: “Addition of diazomethane to.beta.-ethynylpyridines” retrieved from STN, Database accession No. 73:45406, XP002275498, RN 27509-32-6 & Khimiya Geterotsiklicheskikh Soedinenii (1970), (4), 498-502.
Database CA 'Online! Chemical Abstracts Service; Columbus, Ohio, US; Borrachero-Moya, Pastora et al: “Synthesis of 4-(4,6-di-0-benzyl-2,3-dideoxy-.beta.-D-erythro-hex-2-enopyranosyl) pyrazoles from 3,4,6-tri-0-acetyl-D-glucal” retrieved from STN, Database accession No. 129:189545, XP002275499; RNs 211674-08-7, 211674-06-5, 211674-15-6 & Carbohydrate Research (1998), 308(1-2), 181-190.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Baraldi, P.G.. et al: “Synthesis and cardiodepressant activity of dialkyl 1, 4-dihydro-2, 6-dimethyl-4-(pentatomic-heteroaryl)-3, 5-pyridinedicarboxylates, 2” retrieved from STN, Database accession No. 120:289435, XP002275500, RN 154926-87-1 & Drug Design and Discovery (1993), 10(4), 319-29.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Ghosh, Chandra Kanta et al: “Benzopyrans. 31. Reaction of 1,1-diacety1-2-(6-methy1-4-0x0-4H-1-benzopyran-3-yl)ethylene with phenyldiazomethane” retrieved from STN Database accession No. 119:270955, XP002275501 RN 151466-29-4 & Tetrahedron (1993), 49(19), 4135-40.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Moreno-Manas, Marcial. et al: “Hindered rotation around C(sp3) bonds in the enol forms of. alpha.-(9-fluorenyl)-.beta.-diketones and in 3,5-disubstituted 4-(9-fluorenyl)pyrazoles. A proton NMR study” retrieved from STN, Database accession No. 110:74500, XP002275502 RN 118365-08-5 & Bulletin of the Chemical of Japan (1988), 61(5), 1827-9.
Database CA 'Online! Chemical Abstracts Service, Columbus, Ohio, US; Gonzalez, A... et al: “Metal complexes in organic synthesis. Preparation of. Alpha.-(1-adamantyl)-.beta.-dicarbonyl compounds and 4-(1-adamanty1)-3, 5-disubstituted pyrazoles and-1 soxazoles” retrieved from STN, Database accession No. 106:213817, XP002275503 RN 108221-13-2, & Tetrahedron (1986), 42(15), 4253-7.
Database CA 'On
Beswick Mandy Christine
Drysdale Martin James
Dymock Brian William
McDonald Edward
Banner & Witcoff , Ltd.
Bernhardt Emily
Cancer Research Technology Ltd.
The Institute of Cancer Research
Vernalis (Cambridge) Limited
LandOfFree
Pyrazole compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Pyrazole compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pyrazole compounds will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-4104075