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Last Updated: January 27, 2020

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Claims for Patent: 8,691,852

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Summary for Patent: 8,691,852
Title:Amino nicotinic and isonicotinic acid derivatives as DHODH inhibitors
Abstract: The present disclosure relates to compounds of formula (I): ##STR00001## or a pharmaceutically acceptable salt or N-oxide thereof. The present disclosure also relates to pharmaceutical compositions comprising the compounds of formula (I), and to their methods of use in therapy.
Inventor(s): Castro Palomino Laria; Julio Cesar (Barcelona, ES), Erra Sola; Montserrat (Barcelona, ES), Lozoya Toribio; Maria Estrella (Barcelona, ES), Navarro Romero; Eloisa (Barcelona, ES)
Assignee: Amirall, S.A. (Barcelona, ES)
Application Number:13/567,437
Patent Claims:1. A compound of formula (I) ##STR00072## wherein the G.sup.1 groups represent a CR.sup.c group; G.sup.2 is a CR.sup.d group; R.sup.1 is chosen from hydrogen atoms, halogen atoms, C.sub.1-4 alkyl groups, and C.sub.3-8 cycloalkyl groups; R.sup.2 is chosen from hydrogen atoms, halogen atoms, and C.sub.1-4 alkyl groups; R.sup.a is chosen from hydrogen atoms, halogen atoms, and C.sub.1-4 alkyl groups; R.sup.b is chosen from hydrogen atoms and halogen atoms; and R.sup.c is chosen from hydrogen atoms and C.sub.1-4 alkyl groups; R.sup.d is chosen from hydrogen atoms, (OCF.sub.3), and (OCHF.sub.2); G.sup.3 is a nitrogen atom; G.sup.4 is a CH group; and M is a hydrogen atom or an pharmaceutically acceptable cation; or a pharmaceutically acceptable salt or N-oxide thereof.

2. The compound according to claim 1, wherein R.sup.1 is chosen from hydrogen atoms, bromine atoms, chlorine atoms, methyl, and cyclopropyl groups.

3. The compound according to claim 1, wherein each R.sup.c is independently chosen from hydrogen atoms, and methyl groups.

4. The compound according to claim 1, wherein R.sup.d is chosen from hydrogen atoms.

5. The compound according to claim 1, wherein R.sup.a is chosen from hydrogen atoms, fluorine atoms, chlorine atoms, and methyl groups.

6. The compound according to claim 5, wherein R.sup.b is chosen from hydrogen atoms and fluorine atoms.

7. The compound according to claim 1, wherein R.sup.2 is chosen from hydrogen atoms, methyl groups, and halogen atoms.

8. The compound according to claim 7, wherein R.sup.2 is chosen from hydrogen atoms, methyl groups, and chlorine atoms.

9. The compound according to claim 1, wherein R.sup.a is a fluorine atom, R.sup.b is chosen from hydrogen atoms and fluorine atoms, and R.sup.1 is chosen from hydrogen atoms, bromine atoms, chlorine atoms, methyl groups, and cyclopropyl groups.

10. The compound according to claim 9, wherein G.sup.2 is chosen from C C(OCF.sub.3) and C(OCHF.sub.2).

11. The compound according to claim 9, wherein R.sup.c is a hydrogen atom, R.sup.d is chosen from C(OCF.sub.3) and C(OCHF.sub.2), and R.sup.2 is a hydrogen atom.

12. The compound according to claim 11, wherein R.sup.b is a fluorine atom.

13. The compound according to claim 1, chosen from: 2-(2-Methyl-3'-(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(3-Chloro-3'-(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(3-Methyl-3'-(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(3'-(Difluoromethoxy)-3-fluorobiphenyl-4-ylamino)nicotinic acid, 2-(5-Fluoro-2-methyl-3'-(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(2'-chloro-3,5-difluorobiphenyl-4-ylamino)nicotinic acid, 2-(3,5-difluoro-2-methylbiphenyl-4-ylamino)nicotinic acid, 5-cyclopropyl-2-(3,5-difluoro-3'-(trifluoromethoxy)biphenyl-4-ylamino)nic- otinic acid, 2-(2'-chloro-3,5-difluorobiphenyl-4-ylamino)-5-cyclopropylnicotinic acid, 2-(2'-chloro-3,5-difluoro-2-methylbiphenyl-4-ylamino)nicotinic acid, 5-chloro-2-(3,5-difluorobiphenyl-4-ylamino)nicotinic acid, 5-chloro-2-(2'-chloro-3,5-difluorobiphenyl-4-ylamino)nicotinic acid, 2-(3,5-difluoro-2'-methylbiphenyl-4-ylamino)nicotinic acid, 2-(3-Fluoro-3'(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(3,5-Difluoro-3'(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 5-Bromo-2-(3-fluoro-3'-(trifluoromethoxy)biphenyl-4-ylamino)nicotinic acid, 2-(3-Fluoro-3'-(trifluoromethoxy)biphenyl-4-ylamino)-5-methylnicoti- nic acid; or a pharmaceutically acceptable salt or a N-oxide thereof.

14. A method of treating a pathological condition or disease, comprising administering to a mammal in need thereof, an effective amount of a compound according to claim 1, wherein the pathological condition or disease is chosen from rheumatoid arthritis, psoriatic arthritis, and multiple sclerosis.

15. A method of treating a pathological condition or disease, comprising administering to a mammal in need thereof an effective amount of a compound according to claim 1, wherein the pathological condition or disease is chosen from ankylosing spondilytis, Wegener's granulomatosis, systemic lupus erythematosus, psoriasis and sarcoidosis.

16. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable diluent or carrier.

17. A composition comprising (i) a compound according to claim 1; and (ii) another compound chosen from: a) Anti-TNF-alpha monoclonal antibodies; b) TNF-alpha Antagonists; c) Calcineurin (PP-28) Inhibitors/INS Expression Inhibitors; d) IL-1 Receptor Antagonists; e) Anti-CD20 monoclonal antibodies; f) p38 Inhibitors; g) NF-kappa8 (NFK8) Activation Inhibitors; and h) Dihydrofolate Reductase (DHFR) Inhibitors.

18. The composition according to claim 17, wherein: a) the Anti-INF-alpha monoclonal antibody is chosen from Infliximab, Certolizumab pegol, Golimumab, Adalimumab and AME-527; b) the INF-alpha Antagonist is chosen from Etanercept, Lenercept, Onercept and Pegsunercept; c) the Calcineurin (PP-28) Inhibitor INS Expression Inhibitor is chosen from cyclosporine A, Tacrolimus and ISA-247; d) the IL-1 Receptor Antagonist is chosen from Anakinra and AMG-719; the Anti-CD20 monoclonal antibody is chosen from Rituximab, Ofatumumab, Ocrelizumab and TRU-015; f) the p38 Inhibitor is chosen from AMG-548, ARRY-797, Chlormethiazole edisylate, Doramapimod, PS-540446, 38-203580, S8-242235, S8-235699, S8-281832, S8-681323, 38-856553, KC-706, LE0-1606, LE0-15520, SC-80036, SD-06, RWJ-67657, R0-3201195, RO-4402257, AVE-9940, SCI0-323, SCI0-469, TA-5493, and VX-745 and VX-702; g) the NF-kappaB (NFKB) Activation Inhibitor is chosen from Sulfasalazine and Iguratimod; and the Dihydrofolate Reductase (DHFR) Inhibitor is chosen from Methrotexate, Aminopterin and CH-1504.

Summary for Patent:   Start Trial

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
Spain200603250Dec 22, 2006
Spain200701086Apr 23, 2007

Details for Patent 8,691,852

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech RITUXAN rituximab VIAL 103705 001 1997-11-26   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Centocor Inc REMICADE infliximab VIAL 103772 001 1998-08-24   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Immunex ENBREL etanercept VIAL; SUBCUTANEOUS 103795 001 1998-11-02   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Immunex ENBREL etanercept SYRINGE 103795 002 1998-11-02   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Biovitrum Ab KINERET anakinra VIAL; SUBCUTANEOUS 103950 001 2001-11-14   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Biovitrum Ab KINERET anakinra VIAL; SUBCUTANEOUS 103950 002 2001-11-14   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
Biovitrum Ab KINERET anakinra VIAL; SUBCUTANEOUS 103950 003 2001-11-14   Start Trial Amirall, S.A. (Barcelona, ES) 2026-12-22 RX Orphan search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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