Polymorphs of phenyl pyrrole aminoguandium salts

1 . A method of treating a disease or disorder that is an arthritic disease, a kidney disease, a cardiovascular disease, atherosclerosis, a viral disease or disorder, or a systemic inflammatory disorder in a subject in need thereof, said method comprising administering a crystalline Form of the N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium salt to the subject, wherein the crystalline Form of the N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium salt is:

i. a crystalline Form A of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium acetate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu K α radiation at 11.5±0.2, 23.5±0.2, and 27.0±0.2,

ii. a crystalline Form B of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium succinate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 9.7±0.2, 22.8±0.2, and 26.7±0.2,

iii. a crystalline Form C of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium tosylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 14.5±0.2, 21.0±0.2, and 25.2±0.2,

iv. a crystalline Form D of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium fumarate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 17.6±0.2, 21.2±0.2, and 26.3±0.2,

v. a crystalline Form I of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium acetate exhibiting X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 23.5±0.2, 24.2±0.2, and 26.9±0.2,

vi. a crystalline Form II of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium exhibiting X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 13.3±0.2, 21.1±0.2, and 23.1±0.2,

vii. a crystalline Form III of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium napadisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 13.4±0.2, 22.2±0.2, and 26.8±0.2,

viii. a crystalline Form IV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium napadisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 5.4±0.2, 15.6±0.2, and 23.4±0.2,

ix. a crystalline Form V of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium esylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 14.5±0.2, 16.5±0.2, and 18.6±0.2,

x. a crystalline Form VI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium edisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 4.8±0.2, 12.8±0.2, and 16.5±0.2,

xi. a crystalline Form VII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium edisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 6.1±0.2, 15.7±0.2, and 23.6±0.2,

xii. a crystalline Form VIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium edisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 15.5±0.2, 20.7±0.2, and 21.7±0.2,

xiii. a crystalline Form IX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium edisylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 4.5±0.2, 16.7±0.2, and 24.7±0.2,

xiv. a crystalline Form X of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl 1-allylidene}-aminoguanidinium nitrate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 15.3±0.2, 21.4±0.2, and 25.1±0.2,

xv. a crystalline Form XI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium cyclamate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 7.0±0.2, 13.8±0.2, and 15.7±0.2,

xvi. a crystalline Form XII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium cyclamate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 7.3±0.2, 15.3±0.2, and 17.9±0.2,

xvii. a crystalline Form XIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium cyclamate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 15.3±0.2, 18.5±0.2, and 18.7±0.2,

xviii. a crystalline Form XIV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium besylate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 13.0±0.2, 15.1±0.2, and 19.9±0.2,

xix. a crystalline Form XV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium oxalate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 19.5±0.2, 23.3±0.2, and 25.8±0.2,

xx. a crystalline Form XVI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium oxalate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 17.1±0.2, 17.9±0.2, and 19.6±0.2,

xxi. a crystalline Form XVII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium oxalate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 6.3±0.2, 10.6±0.2, and 19.8±0.2,

xxii. a crystalline Form XVIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine (+)-camphor-10-sulfonic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 6.5±0.2, 11.5±0.2, and 14.8±0.2,

xxiii. a crystalline Form XIX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium oxoglutarate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 16.8±0.2, 23.4±0.2, and 23.6±0.2,

xxiv. a crystalline Form XX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine DL-mandelic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 14.8±0.2, 24.2±0.2, and 25.5±0.2,

xxv. a crystalline Form XXI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine DL-mandelic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 5.4±0.2, 10.0±0.2, and 24.6±0.2,

xxvi. a crystalline Form XXII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine hippuric acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 20.1±0.2, 24.1±0.2, and 24.5±0.2,

xxvii. a crystalline Form XXIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium formate exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 13.3±0.2, 15.1±0.2, and 25.6±0.2,

xxviii. a crystalline Form XXIV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine L-lactic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 3.8±0.2, 9.9±0.2, and 11.9±0.2,

xxix. a crystalline Form XXV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine DL-lactic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 9.8±0.2, 11.9±0.2, and 27.6±0.2,

xxx. a crystalline Form XXVI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine glutaric acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 8.3±0.2, 15.9±0.2, and 21.9±0.2,

xxxi. a crystalline Form XXVII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine glutaric acid further exhibiting one or more X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation selected from the group consisting of 16.9±0.2, 25.6±0.2, 27.1±0.2, 28.2±0.2, and 28.7±0.2,

xxxii. a crystalline Form XXVIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine glutaric acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 14.2±0.2, 16.9±0.2, and 24.5±0.2, or

xxxiii. a crystalline Form XXIX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine adipic acid exhibiting at least X-ray lines (2-theta values) in a powder diffraction pattern when measured using Cu Kα radiation at 13.4±0.2, 14.5±0.2, and 25.5±0.2.

2 . The method according to claim 1 , wherein the crystalline Form is:

i. the crystalline Form A of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium acetate,

ii. the crystalline Form B of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium succinate,

iii. the crystalline Form XIV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium besylate,

iv. the crystalline Form XIX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium oxoglutarate,

v. the crystalline Form XX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine DL-mandelic acid,

vi. the crystalline Form XXII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine hippuric acid,

vii. the crystalline Form XXIII of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidinium formate,

viii. the crystalline Form XXIV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine L-lactic acid,

ix. the crystalline Form XXV of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine DL-lactic acid,

x. the crystalline Form XXVI of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine glutaric acid, or

xi the crystalline Form XXIX of N-{3-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]-allylidene}-aminoguanidine adipic acid.

3 . The method according to claim 1 , wherein the arthritic disease is:

i. an auto-immune disease and/or an inflammatory disease that presents with joint inflammation,

ii. inflammatory arthritis,

iii. degenerative arthritis,

iv. metabolic arthritis,

v. reactive arthritis,

vi. infectious arthritis, or

vii. arthritis as part of a systemic inflammatory disease.

4 . The method according to claim 3 , wherein the inflammatory arthritis is Rheumatoid Arthritis.

5 . The method according to claim 4 , wherein said subject is a subject with an inappropriate response to methotrexate (MTX).

6 . The method according to claim 1 , wherein the kidney disease is:

i. kidney disease presenting with proteinuria,

ii. proteinuric kidney disease,

iii glomerular disease,

iv. nephrotic syndrome (glomerulonephrosis),

v. primary nephrotic syndrome (primary glomerulonephrosis),

vi. secondary nephrotic syndrome (secondary glomerulonephrosis),

vii. an inflammatory kidney disease,

viii. glomerulonephritis (GN), or

ix. idiopathic membranous nephropathy (iMN).

7 . The method according to claim 1 , wherein the viral disease or disorder is:

i. a symptomatic viral disease or disorder,

ii. a symptomatic viral disease or disorder with inflammation,

iii. an inflammatory viral disease or disorder,

iv. a viral respiratory infection,

V. a viral respiratory disease or disorder,

vi. a viral disease or disorder of the lung,

vii. a viral disease or disorder with inflammation in the respiratory system,

viii. a viral disease or disorder with one or more respiratory symptoms,

ix. severe disease,

x. critical disease,

xi. viral pneumonia,

xii. viral bronchiolitis,

xiii. viral diseases or disorders with respiratory failure,

xiv. acute respiratory distress syndrome (ARDS),

xv. viral acute respiratory distress syndrome (ARDS),

xvi. symptomatic COVID-19 with acute respiratory distress syndrome (ARDS),

xvii. a viral disease or disorder with systemic inflammatory distress syndrome (SIDS) and/or sepsis,

xviii. a viral disease or disorder with pulmonary insufficiency,

xix. a viral disease or disorder with cytokine release syndrome (CRS) and/or a cytokine storm (hypercytokinemia), or

xx. a viral disease or disorder caused by a viral infection selected from Severe Acute Respiratory Syndrome Corona Virus 2 (SARS-CoV-2); SARS-CoV, MERS-CoV, the dengue virus and influenza virus.

8 . The method according to claim 7 , wherein the influenza virus is Type A, Type B or Type C).