CA2225552A1 - Quinolones and their therapeutic use - Google Patents

Quinolones and their therapeutic use Download PDF

Info

Publication number: CA2225552A1
Authority: CA; Canada
Prior art keywords: ethyl; dihydro; oxo; quinolinecarboxamide; pyridyl
Prior art date: 1995-08-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002225552A

Other languages

English (en)

French (fr)

Inventor

Steven Colin Beasley

John Gary Montana

Hazel Joan Dyke

Alan Findlay Haughan

Karen Ann Runcie

David Thomas Manallack

George Martin Buckley

Robert James Maxey

Hannah Jayne Kendall

Andrew Douglas Baxter

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Darwin Discovery Ltd

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-08-02

Filing date

1996-08-02

Publication date

1997-02-13

1995-08-02 Priority claimed from GBGB9515811.9A external-priority patent/GB9515811D0/en

1995-12-22 Priority claimed from GBGB9526377.8A external-priority patent/GB9526377D0/en

1996-03-20 Priority claimed from GBGB9605868.0A external-priority patent/GB9605868D0/en

1996-06-07 Priority claimed from GBGB9611898.9A external-priority patent/GB9611898D0/en

1996-08-02 Application filed by Individual filed Critical Individual

1997-02-13 Publication of CA2225552A1 publication Critical patent/CA2225552A1/en

Status Abandoned legal-status Critical Current

Links

230000001225 therapeutic effect Effects 0.000 title claims abstract description 5
150000007660 quinolones Chemical class 0.000 title description 2
102000018594 Tumour necrosis factor Human genes 0.000 claims abstract description 25
108050007852 Tumour necrosis factor Proteins 0.000 claims abstract description 25
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 7
230000005764 inhibitory process Effects 0.000 claims abstract description 7
150000001875 compounds Chemical class 0.000 claims description 109
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
-1 C1-6 alkyl amides Chemical class 0.000 claims description 36
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 25
201000010099 disease Diseases 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 9
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 9
206010040070 Septic Shock Diseases 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
206010003246 arthritis Diseases 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
206010017533 Fungal infection Diseases 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims description 6
125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 5
125000005907 alkyl ester group Chemical group 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
210000003979 eosinophil Anatomy 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
239000012453 solvate Substances 0.000 claims description 5
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
206010009900 Colitis ulcerative Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
240000004808 Saccharomyces cerevisiae Species 0.000 claims description 4
206010040047 Sepsis Diseases 0.000 claims description 4
201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
230000002490 cerebral effect Effects 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
206010006458 Bronchitis chronic Diseases 0.000 claims description 3
206010010744 Conjunctivitis allergic Diseases 0.000 claims description 3
206010014824 Endotoxic shock Diseases 0.000 claims description 3
208000031888 Mycoses Diseases 0.000 claims description 3
201000004681 Psoriasis Diseases 0.000 claims description 3
206010063837 Reperfusion injury Diseases 0.000 claims description 3
206010039085 Rhinitis allergic Diseases 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 3
201000010105 allergic rhinitis Diseases 0.000 claims description 3
230000002917 arthritic effect Effects 0.000 claims description 3
125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
206010006451 bronchitis Diseases 0.000 claims description 3
208000007451 chronic bronchitis Diseases 0.000 claims description 3
230000006870 function Effects 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
230000002685 pulmonary effect Effects 0.000 claims description 3
201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 3
230000036303 septic shock Effects 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
208000024827 Alzheimer disease Diseases 0.000 claims description 2
206010006895 Cachexia Diseases 0.000 claims description 2
206010063094 Cerebral malaria Diseases 0.000 claims description 2
206010018367 Glomerulonephritis chronic Diseases 0.000 claims description 2
201000005569 Gout Diseases 0.000 claims description 2
206010018634 Gouty Arthritis Diseases 0.000 claims description 2
208000010496 Heart Arrest Diseases 0.000 claims description 2
206010019617 Henoch-Schonlein purpura Diseases 0.000 claims description 2
208000031814 IgA Vasculitis Diseases 0.000 claims description 2
206010069698 Langerhans' cell histiocytosis Diseases 0.000 claims description 2
208000000112 Myalgia Diseases 0.000 claims description 2
208000018737 Parkinson disease Diseases 0.000 claims description 2
206010044248 Toxic shock syndrome Diseases 0.000 claims description 2
231100000650 Toxic shock syndrome Toxicity 0.000 claims description 2
102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
208000010668 atopic eczema Diseases 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002837 carbocyclic group Chemical group 0.000 claims description 2
230000001684 chronic effect Effects 0.000 claims description 2
201000010064 diabetes insipidus Diseases 0.000 claims description 2
208000003401 eosinophilic granuloma Diseases 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
208000015446 immunoglobulin a vasculitis Diseases 0.000 claims description 2
201000006417 multiple sclerosis Diseases 0.000 claims description 2
201000008383 nephritis Diseases 0.000 claims description 2
201000008482 osteoarthritis Diseases 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
125000002098 pyridazinyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
230000001575 pathological effect Effects 0.000 claims 4
206010012438 Dermatitis atopic Diseases 0.000 claims 3
201000008937 atopic dermatitis Diseases 0.000 claims 3
208000027866 inflammatory disease Diseases 0.000 claims 3
206010039966 Senile dementia Diseases 0.000 claims 2
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
208000018937 joint inflammation Diseases 0.000 claims 2
206010039073 rheumatoid arthritis Diseases 0.000 claims 2
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
LGUCOZFVDDTKDQ-UHFFFAOYSA-N 1-ethyl-4-oxo-n-(2-pyridin-4-ylethyl)-7-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC=C(C(F)(F)F)C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 LGUCOZFVDDTKDQ-UHFFFAOYSA-N 0.000 claims 1
RDHWMVHLPCKHTK-UHFFFAOYSA-N 1-ethyl-n-[2-(4-methoxyphenyl)ethyl]-4-oxo-6-(trifluoromethyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(C(F)(F)F)=CC=C2N(CC)C=C1C(=O)NCCC1=CC=C(OC)C=C1 RDHWMVHLPCKHTK-UHFFFAOYSA-N 0.000 claims 1
RWQUYEFZTSWDNB-UHFFFAOYSA-N 5-ethyl-8-oxo-n-(2-pyridin-4-ylethyl)-[1,3]dioxolo[4,5-g]quinoline-7-carboxamide Chemical compound O=C1C2=CC=3OCOC=3C=C2N(CC)C=C1C(=O)NCCC1=CC=NC=C1 RWQUYEFZTSWDNB-UHFFFAOYSA-N 0.000 claims 1
208000030507 AIDS Diseases 0.000 claims 1
206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
206010020649 Hyperkeratosis Diseases 0.000 claims 1
206010061218 Inflammation Diseases 0.000 claims 1
208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
206010022562 Intermittent claudication Diseases 0.000 claims 1
208000001126 Keratosis Diseases 0.000 claims 1
208000005314 Multi-Infarct Dementia Diseases 0.000 claims 1
208000006011 Stroke Diseases 0.000 claims 1
206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
208000024780 Urticaria Diseases 0.000 claims 1
201000004810 Vascular dementia Diseases 0.000 claims 1
238000009825 accumulation Methods 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
208000019664 bone resorption disease Diseases 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
230000004054 inflammatory process Effects 0.000 claims 1
208000021156 intermittent vascular claudication Diseases 0.000 claims 1
208000032839 leukemia Diseases 0.000 claims 1
201000004792 malaria Diseases 0.000 claims 1
206010027175 memory impairment Diseases 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
RSMFTGCPHSMCLE-UHFFFAOYSA-N quinoline-7-carboxamide hydrochloride Chemical compound C1=CC2=C(C=C(C=C2)C(=O)N)N=C1.Cl RSMFTGCPHSMCLE-UHFFFAOYSA-N 0.000 claims 1
201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 1
201000005539 vernal conjunctivitis Diseases 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
238000000034 method Methods 0.000 description 21
239000002253 acid Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
241000700605 Viruses Species 0.000 description 13
239000000243 solution Substances 0.000 description 12
KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 description 11
229960000321 oxolinic acid Drugs 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
210000001744 T-lymphocyte Anatomy 0.000 description 9
239000007787 solid Substances 0.000 description 8
208000031886 HIV Infections Diseases 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
230000002401 inhibitory effect Effects 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 6
239000003981 vehicle Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
208000037357 HIV infectious disease Diseases 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
239000006071 cream Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000000499 gel Substances 0.000 description 4
208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
230000010076 replication Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
230000006433 tumor necrosis factor production Effects 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
108090000695 Cytokines Proteins 0.000 description 3
102000004127 Cytokines Human genes 0.000 description 3
241000701022 Cytomegalovirus Species 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
241000713340 Human immunodeficiency virus 2 Species 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
230000004913 activation Effects 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
238000003556 assay Methods 0.000 description 3
239000002585 base Substances 0.000 description 3
125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
239000002158 endotoxin Substances 0.000 description 3
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 3
238000011049 filling Methods 0.000 description 3
230000014509 gene expression Effects 0.000 description 3
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 3
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 3
239000006210 lotion Substances 0.000 description 3
210000001616 monocyte Anatomy 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000008569 process Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
JWEQRJSCTFBRSI-PCLIKHOPSA-N rboxylate Chemical compound COC(=O)C1C(N2C3=O)C4=CC=CC=C4OC1(C)N=C2S\C3=C\C(C=1)=CC=C(OC)C=1COC1=CC=CC=C1C JWEQRJSCTFBRSI-PCLIKHOPSA-N 0.000 description 3
239000000600 sorbitol Substances 0.000 description 3
235000010356 sorbitol Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
230000029812 viral genome replication Effects 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
206010001513 AIDS related complex Diseases 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
206010003645 Atopy Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
208000035473 Communicable disease Diseases 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
206010020164 HIV infection CDC Group III Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
201000002661 Spondylitis Diseases 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
230000006044 T cell activation Effects 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
102100040247 Tumor necrosis factor Human genes 0.000 description 2
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
208000036142 Viral infection Diseases 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000009471 action Effects 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
229940095074 cyclic amp Drugs 0.000 description 2
230000007812 deficiency Effects 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
230000009429 distress Effects 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
239000000945 filler Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
206010022000 influenza Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000000670 limiting effect Effects 0.000 description 2
229920006008 lipopolysaccharide Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000002540 macrophage Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000000241 respiratory effect Effects 0.000 description 2
210000002345 respiratory system Anatomy 0.000 description 2
239000007921 spray Substances 0.000 description 2
229910021653 sulphate ion Inorganic materials 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
239000012049 topical pharmaceutical composition Substances 0.000 description 2
241000701161 unidentified adenovirus Species 0.000 description 2
230000009385 viral infection Effects 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
IDLHTECVNDEOIY-UHFFFAOYSA-N 2-pyridin-4-ylethanamine Chemical compound NCCC1=CC=NC=C1 IDLHTECVNDEOIY-UHFFFAOYSA-N 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
102000001381 Arachidonate 5-Lipoxygenase Human genes 0.000 description 1
108010093579 Arachidonate 5-lipoxygenase Proteins 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
208000006386 Bone Resorption Diseases 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000543381 Cliftonia monophylla Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000283073 Equus caballus Species 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000282324 Felis Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
102000003886 Glycoproteins Human genes 0.000 description 1
208000009889 Herpes Simplex Diseases 0.000 description 1
208000007514 Herpes zoster Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical group C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
108010002352 Interleukin-1 Proteins 0.000 description 1
108090001005 Interleukin-6 Proteins 0.000 description 1
HUYWAWARQUIQLE-UHFFFAOYSA-N Isoetharine Chemical compound CC(C)NC(CC)C(O)C1=CC=C(O)C(O)=C1 HUYWAWARQUIQLE-UHFFFAOYSA-N 0.000 description 1
241000713666 Lentivirus Species 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
108010050619 Monokines Proteins 0.000 description 1
102000013967 Monokines Human genes 0.000 description 1
101100202896 Mus musculus Selenoo gene Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
208000030852 Parasitic disease Diseases 0.000 description 1
241001494479 Pecora Species 0.000 description 1
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 1
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
101150057388 Reln gene Proteins 0.000 description 1
206010038997 Retroviral infections Diseases 0.000 description 1
201000010001 Silicosis Diseases 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
239000004141 Sodium laurylsulphate Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
241000713325 Visna/maedi virus Species 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000011149 active material Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000001919 adrenal effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
HXXFSFRBOHSIMQ-VFUOTHLCSA-N alpha-D-glucose 1-phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O HXXFSFRBOHSIMQ-VFUOTHLCSA-N 0.000 description 1
230000001668 ameliorated effect Effects 0.000 description 1
238000005576 amination reaction Methods 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000008512 biological response Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
230000024279 bone resorption Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
230000003177 cardiotonic effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
230000020411 cell activation Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
229960000258 corticotropin Drugs 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
ZOOGRGPOEVQQDX-UHFFFAOYSA-N cyclic GMP Natural products O1C2COP(O)(=O)OC2C(O)C1N1C=NC2=C1NC(N)=NC2=O ZOOGRGPOEVQQDX-UHFFFAOYSA-N 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000002702 enteric coating Substances 0.000 description 1
238000009505 enteric coating Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
ZQSXVXUZVAFZCO-UHFFFAOYSA-N ethyl 6-fluoro-4-oxo-1-(pyridin-4-ylmethyl)quinoline-3-carboxylate Chemical compound C12=CC=C(F)C=C2C(=O)C(C(=O)OCC)=CN1CC1=CC=NC=C1 ZQSXVXUZVAFZCO-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000374 eutectic mixture Substances 0.000 description 1
230000003090 exacerbative effect Effects 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000002538 fungal effect Effects 0.000 description 1
229950010772 glucose-1-phosphate Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002458 infectious effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229960001268 isoetarine Drugs 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
208000011379 keloid formation Diseases 0.000 description 1
210000001865 kupffer cell Anatomy 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
230000002969 morbid Effects 0.000 description 1
210000004165 myocardium Anatomy 0.000 description 1
210000000822 natural killer cell Anatomy 0.000 description 1
230000007302 negative regulation of cytokine production Effects 0.000 description 1
210000004498 neuroglial cell Anatomy 0.000 description 1
GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
229940055577 oleyl alcohol Drugs 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
244000045947 parasite Species 0.000 description 1
239000003182 parenteral nutrition solution Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
229960005205 prednisolone Drugs 0.000 description 1
OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
AMMGCGVWJMRTQI-UHFFFAOYSA-N prop-1-en-2-yl carbonochloridate Chemical compound CC(=C)OC(Cl)=O AMMGCGVWJMRTQI-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000004044 response Effects 0.000 description 1
229960002052 salbutamol Drugs 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
238000007789 sealing Methods 0.000 description 1
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
229940032147 starch Drugs 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000002278 tabletting lubricant Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
230000009772 tissue formation Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000759 toxicological effect Toxicity 0.000 description 1
150000003852 triazoles Chemical class 0.000 description 1
229940046728 tumor necrosis factor alpha inhibitor Drugs 0.000 description 1
239000002451 tumor necrosis factor inhibitor Substances 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Diabetes (AREA)
Epidemiology (AREA)
Hematology (AREA)
Physical Education & Sports Medicine (AREA)
Pulmonology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Rheumatology (AREA)
Immunology (AREA)
Orthopedic Medicine & Surgery (AREA)
Communicable Diseases (AREA)
Obesity (AREA)
Oncology (AREA)
Endocrinology (AREA)
Dermatology (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Virology (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)

CA002225552A 1995-08-02 1996-08-02 Quinolones and their therapeutic use Abandoned CA2225552A1 (en)

Applications Claiming Priority (8)

Application Number	Priority Date	Filing Date	Title
GB9515811.9		1995-08-02
GBGB9515811.9A GB9515811D0 (en)	1995-08-02	1995-08-02	Novel compounds
GBGB9526377.8A GB9526377D0 (en)	1995-12-22	1995-12-22	Novel compounds
GB9526377.8		1995-12-22
GBGB9605868.0A GB9605868D0 (en)	1996-03-20	1996-03-20	Novel compounds
GB9605868.0		1996-03-20
GBGB9611898.9A GB9611898D0 (en)	1996-06-07	1996-06-07	Quinolones and their therapeutic use
GB9611898.9		1996-06-07

Publications (1)

Publication Number	Publication Date
CA2225552A1 true CA2225552A1 (en)	1997-02-13

Family

ID=27451319

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002225552A Abandoned CA2225552A1 (en)	1995-08-02	1996-08-02	Quinolones and their therapeutic use

Country Status (12)

Country	Link
US (1)	US5891878A (2)
EP (1)	EP0841929B1 (2)
JP (1)	JPH11513021A (2)
AT (1)	ATE239477T1 (2)
AU (1)	AU696390B2 (2)
CA (1)	CA2225552A1 (2)
DE (1)	DE69628019T2 (2)
DK (1)	DK0841929T3 (2)
ES (1)	ES2193252T3 (2)
MX (1)	MX9800922A (2)
PT (1)	PT841929E (2)
WO (1)	WO1997004779A1 (2)

Families Citing this family (51)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6077850A (en) *	1997-04-21	2000-06-20	G.D. Searle & Co.	Substituted benzopyran analogs for the treatment of inflammation
IT1296985B1 (it) *	1997-12-19	1999-08-03	Zambon Spa	Derivati benzazinici inibitori della fosfodiesterasi 4
DE69831506T2 (de) *	1997-12-22	2006-06-29	Pharmacia & Upjohn Co. Llc, Kalamazoo	4-hydroxychinolin-3-carboxamide und hydrazide als antivirale wirkstoffe
IT1302677B1 (it)	1998-10-15	2000-09-29	Zambon Spa	Derivati benzazinici inibitori della fosfodiesterasi 4
US6248736B1 (en)	1999-01-08	2001-06-19	Pharmacia & Upjohn Company	4-oxo-1,4-dihydro-3-quinolinecarboxamides as antiviral agents
US6248739B1 (en) *	1999-01-08	2001-06-19	Pharmacia & Upjohn Company	Quinolinecarboxamides as antiviral agents
EP1212089B1 (en)	1999-08-21	2006-03-22	ALTANA Pharma AG	Synergistic combination of roflumilast and salmeterol
US6436971B2 (en) *	2000-02-09	2002-08-20	Smithkline Beecham Corporation	Use of PDE 4-specific inhibitors to reduce the severity of a bacterial infection after a respiratory viral infection
JP2003531195A (ja)	2000-03-21	2003-10-21	ファルマシア・アンド・アップジョン・カンパニー	抗ウイルス剤としての４−ヒドロキシシンノリン−３−カルボキサミド
NZ521522A (en)	2000-03-21	2004-08-27	Upjohn Co	4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxamides useful as antiviral agents
CA2399991A1 (en)	2000-03-21	2001-09-27	Pharmacia & Upjohn Company	4-hydroxy-1,8-naphthyridine-3-carboxamides as antiviral agents
JP2003528087A (ja)	2000-03-21	2003-09-24	ファルマシア・アンド・アップジョン・カンパニー	抗ウイルス剤としての４−オキソ−１，４−ジヒドロ−３−シンノリンカルボキサミド
PE20011349A1 (es)	2000-06-16	2002-01-19	Upjohn Co	1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales
US6559145B2 (en)	2000-07-12	2003-05-06	Pharmacia & Upjohn Company	Heterocycle carboxamides as antiviral agents
US6562822B2 (en)	2000-07-12	2003-05-13	Pharmacia & Upjohn Company	Heterocyle carboxamides as antiviral agents
US6730682B2 (en) *	2000-07-12	2004-05-04	Pharmacia & Upjohn Company	Heterocycle carboxamides as antiviral agents
TWI243164B (en)	2001-02-13	2005-11-11	Aventis Pharma Gmbh	Acylated indanyl amines and their use as pharmaceuticals
PE20020856A1 (es) *	2001-02-13	2002-11-11	Aventis Pharma Gmbh	1,2,3,4-tetrahidronaftil aminas aciladas
US6544990B2 (en)	2001-03-01	2003-04-08	Pharmacia & Upjohn Company	Substituted quinolinecarboxamides as antiviral agents
BR0212864A (pt) *	2001-09-26	2004-08-17	Bayer Pharmaceuticals Corp	Derivados de 1,6-naftiridina como antidiabéticos
DE60311779T2 (de) *	2002-04-01	2007-11-22	University of Florida Research Foundation, Inc., Gainesville	Steroidale Chinole als Prodrugs von Antioxidantien
US7300926B2 (en) *	2002-04-01	2007-11-27	University Of Florida Research Foundation, Inc.	Steroidal quinols and their use for estrogen replacement therapy
US20070213310A1 (en) *	2002-04-01	2007-09-13	Laszlo Prokai	Prodrugs for Use as Ophthalmic Agents
US7186707B2 (en)	2002-04-01	2007-03-06	University Of Florida	Prodrugs for use as ophthalmic agents
EP1569648A4 (en) *	2002-12-09	2006-10-04	Univ Florida	PRODRUGS FOR OPHTHALMIKA
MXPA05010373A (es)	2003-04-01	2005-12-05	Applied Research Systems	Inhibidores de fosfodiesterasas en infertilidad.
WO2005009971A1 (ja)	2003-07-24	2005-02-03	Astellas Pharma Inc.	キノロン誘導体又はその塩
US7470706B2 (en) *	2004-01-31	2008-12-30	Sanofi-Aventis Deutschland Gmbh	Cycloalkyl-substituted 7-amino-4-quinolone-3-carboxylic acid derivatives, process for their preparation and their use as medicaments
DE102004004971B3 (de) *	2004-01-31	2005-09-15	Aventis Pharma Deutschland Gmbh	Cycloalkyl substituierte 7-Amino-4-chinolon-3-carbonsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arnzeimittel
JP4775259B2 (ja)	2004-03-31	2011-09-21	味の素株式会社	アニリン誘導体
RS56037B1 (sr)	2004-06-24	2017-09-29	Vertex Pharma	Modulatori atp-vezujućih kasetnih transportera
EP2502914A3 (en) *	2004-06-24	2013-12-04	Vertex Pharmaceuticals Incorporated	Modulators of ATP-binding cassette transporters
RU2556984C2 (ru) *	2004-06-24	2015-07-20	Вертекс Фармасьютикалз Инкорпорейтед	Модуляторы транспортеров атф-связывающей кассеты
US8354427B2 (en)	2004-06-24	2013-01-15	Vertex Pharmaceutical Incorporated	Modulators of ATP-binding cassette transporters
DE102004035203A1 (de) *	2004-07-21	2006-02-16	Bayer Healthcare Ag	Substituierte Chinolone
DE102005030524A1 (de)	2005-06-30	2007-01-18	Aicuris Gmbh & Co. Kg	Substituierte Chinolone II
EP1979367A2 (en) *	2005-12-24	2008-10-15	Vertex Pharmaceuticals Incorporated	Quinolin-4-one derivatives as modulators of abc transporters
AU2006331565A1 (en) *	2005-12-27	2007-07-05	Vertex Pharmaceuticals Incorporated	Compounds useful in CFTR assays and methods therewith
EP3219705B1 (en)	2005-12-28	2020-03-11	Vertex Pharmaceuticals Incorporated	Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide
DE102006005861A1 (de)	2006-02-09	2007-08-23	Aicuris Gmbh & Co. Kg	Substituierte Chinolone III
AU2007225088B2 (en) *	2006-03-13	2012-09-13	Kyorin Pharmaceutical Co., Ltd	Aminoquinolones as GSK-3 inhibitors
US12458635B2 (en)	2008-08-13	2025-11-04	Vertex Pharmaceuticals Incorporated	Pharmaceutical composition and administrations thereof
US20100074949A1 (en)	2008-08-13	2010-03-25	William Rowe	Pharmaceutical composition and administration thereof
EP2349263B1 (en)	2008-10-23	2014-04-23	Vertex Pharmaceuticals Inc.	Modulators of cystic fibrosis transmembrane conductance regulator
PL2408750T3 (pl)	2009-03-20	2016-02-29	Vertex Pharma	Sposób otrzymywania modulatorów błonowego regulatora przewodnictwa swoistego dla mukowiscydozy
US8802700B2 (en)	2010-12-10	2014-08-12	Vertex Pharmaceuticals Incorporated	Modulators of ATP-Binding Cassette transporters
JP2015511583A (ja)	2012-02-27	2015-04-20	バーテックスファーマシューティカルズインコーポレイテッドＶｅｒｔｅｘＰｈａｒｍａｃｅｕｔｉｃａｌｓＩｎｃｏｒｐｏｒａｔｅｄ	薬学的組成物およびその投与
GB201409044D0 (en)	2014-05-21	2014-07-02	Ucl Business Plc	New compounds
CN107250113B (zh)	2014-10-07	2019-03-29	弗特克斯药品有限公司	囊性纤维化跨膜传导调节蛋白的调节剂的共晶
CN107998131B (zh) *	2017-12-27	2019-09-24	湖北工业大学	芳香酯类化合物用于制备抗adv-7病毒药物
CN111646941A (zh) *	2020-07-17	2020-09-11	天津科技大学	一种磺酰胺类衍生物及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3524558A (en) *	1967-03-30	1970-08-18	American Mach & Foundry	Cargo loading means and method
US3524858A (en) *	1967-05-18	1970-08-18	Warner Lambert Pharmaceutical	1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid
FR2564832B1 (fr) *	1984-05-23	1987-05-15	Panmedica Sa	Nouveaux n-acyl derives d'amino-acides et leurs esters, leur procede de preparation et medicaments les contenant
US4786644A (en) *	1987-11-27	1988-11-22	Hoechst-Roussel Pharmaceuticals Inc.	1-aryl-3-quinolinecarboxamide
JPH02124871A (ja) *	1988-07-27	1990-05-14	Dainippon Pharmaceut Co Ltd	１位が置換された複素環式カルボン酸アミド誘導体

1996
- 1996-08-02 AU AU66263/96A patent/AU696390B2/en not_active Ceased
- 1996-08-02 AT AT96925905T patent/ATE239477T1/de not_active IP Right Cessation
- 1996-08-02 JP JP9507373A patent/JPH11513021A/ja not_active Ceased
- 1996-08-02 WO PCT/GB1996/001862 patent/WO1997004779A1/en not_active Ceased
- 1996-08-02 ES ES96925905T patent/ES2193252T3/es not_active Expired - Lifetime
- 1996-08-02 EP EP96925905A patent/EP0841929B1/en not_active Expired - Lifetime
- 1996-08-02 CA CA002225552A patent/CA2225552A1/en not_active Abandoned
- 1996-08-02 DK DK96925905T patent/DK0841929T3/da active
- 1996-08-02 DE DE69628019T patent/DE69628019T2/de not_active Expired - Fee Related
- 1996-08-02 MX MX9800922A patent/MX9800922A/es not_active IP Right Cessation
- 1996-08-02 US US08/691,338 patent/US5891878A/en not_active Expired - Fee Related
- 1996-08-02 PT PT96925905T patent/PT841929E/pt unknown

Also Published As

Publication number	Publication date
DE69628019D1 (de)	2003-06-12
AU6626396A (en)	1997-02-26
EP0841929A1 (en)	1998-05-20
DE69628019T2 (de)	2004-01-22
MX9800922A (es)	1998-05-31
US5891878A (en)	1999-04-06
JPH11513021A (ja)	1999-11-09
PT841929E (pt)	2003-09-30
WO1997004779A1 (en)	1997-02-13
ATE239477T1 (de)	2003-05-15
ES2193252T3 (es)	2003-11-01
AU696390B2 (en)	1998-09-10
EP0841929B1 (en)	2003-05-07
DK0841929T3 (da)	2003-09-01

Legal Events

Date	Code	Title	Description
2003-07-28	EEER	Examination request
2007-08-02	FZDE	Discontinued

Publication	Publication Date	Title
CA2225552A1 (en)	1997-02-13	Quinolones and their therapeutic use
EP0841927B1 (en)	2004-01-28	Quinolones and their therapeutic use
US5728712A (en)	1998-03-17	3,4-disubstituted-phenylsulphonamides and their therapeutic use
US5821366A (en)	1998-10-13	Xanthines and their therapeutic use
EP1045690B1 (en)	2003-04-23	Benzenesulfonamide inhibitors of pde-iv and their therapeutic use
US5919789A (en)	1999-07-06	Xanthines and their therapeutic use
AU710876B2 (en)	1999-09-30	Quinolones and their therapeutic use
EP0946541B1 (en)	2003-07-30	Quinolines and their therapeutic use
WO1996036596A1 (en)	1996-11-21	3,4-disubstituted-phenylsulphonamides and their therapeutic use
WO1997030999A1 (en)	1997-08-28	Quinolones and their therapeutic use
WO2014210319A2 (en)	2014-12-31	Inhibitors of plasmodium falciparum equilibrative nucleoside transporter type 1 as anti-parasitic compounds
HUP9903797A2 (hu)	2001-04-28	Benzofurán-karboxamidok és -szulfonamidok, alkalmazásuk gyógyszerkészítmények előállítására és ezek a gyógyszerkészítmények
AU735573B2 (en)	2001-07-12	Quinoline derivatives as PDE IV and/or TNF inhibitors
US5792774A (en)	1998-08-11	Quinolones and their therapeutic use
KR20010033842A (ko)	2001-04-25	티엔에프 및 피디이-ⅳ 억제 활성을 갖는 헤테로시클릭화합물의 엔-옥사이드
EP0428105B1 (en)	1994-01-19	Use of quinolyl- and isoquinolyloxazole-2-ones for the production of a medicament for the prevention of glycoprotein enveloped virus infectivity
MXPA97008903A (en)	1998-10-15	Xantinas and its use terapeut