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US 2010/0168077 A1Published application
Novel Pyridine Derivatives, Processes for Preparing Them, Pharmaceutical Compositions Thereof
AssigneeUCB Pharma S.A.
InventorDuncan Hannah
Life of this patent
Estimating the term…
Abstract
The present invention concerns 2-amino pyridine derivatives of formula 1 processes for preparing them, pharmaceutical compositions containing them and their use as pharmaceuticals.
Claims23
A compound having formula I or pharmaceutically acceptable salts thereof or stereoisomeric forms thereof, and the geometrical isomers, enantiomers, diastereoisomers, and pharmaceutically acceptable salts thereof
- * represents the point of attachment to the rest of the molecule
- wherein:
- B is aryl optionally substituted with a substituent selected from the group consisting of C1-6 alkyl, halogen, C1-3 haloalkyl, hydroxyl, C1-3 alkoxy, C1-3 haloalkoxy, carboxylic acid, ester, C1-3 alkylsulfonyl, amide, sulfonamide, C1-3 dialkylamine, 3-10 member heterocycloalkyl, heteroaryl;
- or B is a heteroaryl ring optionally substituted with a substituent selected from the group consisting of C1-6 alkyl, halogen, C1-3 haloalkyl, hydroxyl, C1-3 alkoxy, C1-3 haloalkoxy, carboxylic acid, ester, C1-3 alkylsulfonyl, amide, sulfonamide, C1-3 dialkylamine, 3-10 member heterocycloalkyl, heteroaryl;
- or is C1-6 alkyl optionally substituted with a substituent selected from the group consisting of aryl, heteroaryl, 3-10 member cycloalkyl, 3-10 member heterocycloalkyl, hydroxyl, C1-3 alkoxy, C1-3 haloalkoxy, carboxylic acid, ester, C1-3 alkylsulfonyl, amide, sulfonamide, C1-3 dialkylamine;
- or B is C2-6 alkenyl optionally substituted with a substituent selected from the group consisting of C1-6 alkyl, aryl, heteroaryl, 3-10 member cycloalkyl, 3-10 member heterocycloalkyl, hydroxyl, C1-3 alkoxy, C1-3 haloalkoxy, carboxylic acid, ester, C1-3 alkylsulfonyl, amide, sulfonamide, C1-3 dialkylamine;
- or B is C3-10 cycloalkyl optionally substituted by C1-6 alkyl;
- or B is C3-10 cycloalkenyl optionally substituted by C1-6 alkyl;
- or B is a group of formula II
- wherein
- Rb is hydrogen or C1-6 alkyl;
- Rc is C3-10 cycloalkyl optionally substituted by C1-3 alkyl;
- or Rb and Rc can form together with the nitrogen, a 3-10 member heterocycloalkyl or a heteroaryl optionally substituted by C1-6 alkyl;
- D is a group of formula III
- wherein
- Ra is hydrogen or unsubstituted C1-3 alkyl;
- p is 1 or 2 or 3;
- Y is a group of formula IV
- wherein
- Rd is hydrogen or unsubstituted C1-3 alkyl;
- Re is hydrogen or unsubstituted C1-3 alkyl;
- Rf is hydrogen or unsubstituted C1-3 alkyl;
- or Y is a group of formula V
- N—Rg formula V
- wherein
- Rg is hydrogen or unsubstituted C1-3 alkyl;
- or D is a group of formula VI
- wherein
- Rh is hydrogen or unsubstituted C1-3 alkyl;
- Ri is hydrogen or unsubstituted C1-3 alkyl;
- or D is a group of formula VII
- wherein
- q is 1 or 2 or 3;
- Rk is hydrogen or unsubstituted C1-3 alkyl;
- Rl is hydrogen or unsubstituted C1-3 alkyl;
- Rm is hydrogen or unsubstituted C1-3 alkyl;
- or D is group of formula VIII
- wherein
- r is 1 or 2;
- Rn is hydrogen or unsubstituted C1-3 alkyl;
- Ro is hydrogen or unsubstituted C1-3 alkyl;
- Rp is hydrogen or unsubstituted C1-3 alkyl;
- or D is a group of formula IX
- or D is a group of formula X
- wherein
- Rq is hydrogen or unsubstituted C1-3 alkyl;
- or D is a group of formula XI
- wherein
- Rr is hydrogen or unsubstituted C1-3 alkyl;
- Rs is hydrogen or unsubstituted C1-3 alkyl;
- s is 1 or 2
- t is 1 or 2;
- or D is a group of formula XII
- wherein
- Rt is hydrogen or unsubstituted C1-3 alkyl.
52 more elements
Synthesis intermediates selected from a group consisting of:
- 2,6-difluoro-4-(4-methylpiperazinyl)pyridine;
- 2-fluoro-4-(4-methylpiperazinyl)-6-(4-methoxybenzylamino)pyridine;
- 2,6-difluoro-4-((3-N-methyl-N-tertbutoxycarbonylamino)pyrrolidino)-pyridine;
- 2-(4-methoxybenzylamino)-4-((3-N-methyl-N-tertbutoxycarbonylamino)pyrrolidino)-6-fluoropyridine;
- 2,6-dibromo-4-((3-tertbutoxycarbonylamino)pyrrolidino)-pyridine;
- 2-bromo-4-((3-N-methyl,N-tertbutoxycarbonylamino)pyrrolidino)-6-(4-methoxybenzylamino-pyridine;
- 2,6-dichloro-4-((N-tertbutoxycarbonylamino)pyrrolidino)pyridine;
- 2-chloro-6-(4-methoxybenzylamino)-4-((N-tertbutoxycarbonylamino)pyrrolidino)pyridine;
- 2-chloro-4-(4-methylpiperazin-1-yl)-6-(4-methoxybenzylamino)pyridine;
- 2-(2-adamantyl)-4-(4-methylpiperazin-1-yl)-6-(4-methoxybenzylamino)pyridine.
7 more elements
(canceled)
The method of claim 21 wherein the H4 dependent disease is adult respiratory distress syndrome, acute respiratory distress syndrome, bronchitis, chronic bronchitis, chronic obstructive pulmonary disease, cystic fibrosis, asthma, emphysema, rhinitis, chronic sinusitis, allergy, allergy induced airway responses, allergic rhinitis, viral rhinitis, non-allergic rhinitis, perennial and seasonal rhinitis, nasal congestion, allergic congestion;
- female and male sexual dysfunction, overactive bladder conditions, urinary incontinence, neurogenic detrusor overactivity, idiopathic detrusor overactivity, benign prostate hyperplasia and lower urinary tract symptoms;
- dermatological diseases such as dermatitis and psoriasis and treatment of itchy skin;
- thromboembolic diseases, atherosclerosis, myocardial infarction, angina pectoris, (unstable angina) myocardial ischaemia and arrhythmia, reocclusions and restenosis following angioplasty or coronary bypass, stroke, transitory ischaemic attacks, peripheral arterial occlusive diseases, pulmonary embolisms or deep venous thromboses, hypotension, pulmonary hypertension, malignant hypertension, cardiac insufficiency, heart or kidney failure, stroke and renal dysfunction;
- diseases of the gastrointestinal tract including inflammatory bowel disease, Crohn's disease, ulcerative colitis;
- autoimmune diseases including rheumatoid arthritis, multiple sclerosis;
- cancer;
- pain;
- or lymphatic diseases.
5 more elements
-24. (canceled)
Dependencies are inferred from the claim text.