ZA200100229B - FKBP inhibitors. - Google Patents
FKBP inhibitors. Download PDFInfo
- Publication number
- ZA200100229B ZA200100229B ZA200100229A ZA200100229A ZA200100229B ZA 200100229 B ZA200100229 B ZA 200100229B ZA 200100229 A ZA200100229 A ZA 200100229A ZA 200100229 A ZA200100229 A ZA 200100229A ZA 200100229 B ZA200100229 B ZA 200100229B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- substance according
- optionally substituted
- halo
- disease
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title description 4
- 108010027179 Tacrolimus Binding Proteins Proteins 0.000 title description 2
- 102000018679 Tacrolimus Binding Proteins Human genes 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 53
- 239000000126 substance Substances 0.000 claims description 52
- 125000001424 substituent group Chemical group 0.000 claims description 42
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 208000012902 Nervous system disease Diseases 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 210000003169 central nervous system Anatomy 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 206010012601 diabetes mellitus Diseases 0.000 claims description 12
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- -1 phenyloxy, benzyloxy Chemical group 0.000 claims description 10
- 230000006378 damage Effects 0.000 claims description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 208000025966 Neurological disease Diseases 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 206010012289 Dementia Diseases 0.000 claims description 7
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 7
- 230000000508 neurotrophic effect Effects 0.000 claims description 7
- 208000016621 Hearing disease Diseases 0.000 claims description 6
- 208000026072 Motor neurone disease Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 208000009205 Tinnitus Diseases 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 201000006417 multiple sclerosis Diseases 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 230000007971 neurological deficit Effects 0.000 claims description 6
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
- 230000000750 progressive effect Effects 0.000 claims description 6
- 210000000278 spinal cord Anatomy 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 231100000886 tinnitus Toxicity 0.000 claims description 6
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 230000000472 traumatic effect Effects 0.000 claims description 5
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 208000037859 AIDS-related disorder Diseases 0.000 claims description 3
- 241000238876 Acari Species 0.000 claims description 3
- 206010003591 Ataxia Diseases 0.000 claims description 3
- 206010003694 Atrophy Diseases 0.000 claims description 3
- 208000006373 Bell palsy Diseases 0.000 claims description 3
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 3
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 3
- 208000003435 Optic Neuritis Diseases 0.000 claims description 3
- 208000024777 Prion disease Diseases 0.000 claims description 3
- 206010038923 Retinopathy Diseases 0.000 claims description 3
- 206010041591 Spinal osteoarthritis Diseases 0.000 claims description 3
- 208000036826 VIIth nerve paralysis Diseases 0.000 claims description 3
- 201000011101 acute retrobulbar neuritis Diseases 0.000 claims description 3
- 230000037444 atrophy Effects 0.000 claims description 3
- 230000001363 autoimmune Effects 0.000 claims description 3
- 150000001540 azides Chemical class 0.000 claims description 3
- 229960000860 dapsone Drugs 0.000 claims description 3
- 201000000585 muscular atrophy Diseases 0.000 claims description 3
- 206010028417 myasthenia gravis Diseases 0.000 claims description 3
- 210000000653 nervous system Anatomy 0.000 claims description 3
- 210000001328 optic nerve Anatomy 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 208000022670 retrobulbar neuritis Diseases 0.000 claims description 3
- 208000002320 spinal muscular atrophy Diseases 0.000 claims description 3
- 208000005801 spondylosis Diseases 0.000 claims description 3
- 206010048627 thoracic outlet syndrome Diseases 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 3
- WXMNXZYSBAJBKT-ZDUSSCGKSA-N (2s)-1-(5-chloro-1,3-benzoxazol-2-yl)-2-methylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@]1(C)CCCN1C1=NC2=CC(Cl)=CC=C2O1 WXMNXZYSBAJBKT-ZDUSSCGKSA-N 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
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 201000006938 muscular dystrophy Diseases 0.000 claims description 2
- 230000009689 neuronal regeneration Effects 0.000 claims description 2
- 201000001119 neuropathy Diseases 0.000 claims description 2
- 230000007823 neuropathy Effects 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 230000008929 regeneration Effects 0.000 claims description 2
- 238000011069 regeneration method Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- 208000005264 motor neuron disease Diseases 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 208000036319 cervical spondylosis Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000003387 muscular Effects 0.000 claims 1
- 230000001537 neural effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 239000012038 nucleophile Substances 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 239000002253 acid Substances 0.000 description 5
- 108010016648 Immunophilins Proteins 0.000 description 4
- 102000000521 Immunophilins Human genes 0.000 description 4
- 101710147152 Peptidyl-prolyl cis-trans isomerase FKBP4 Proteins 0.000 description 4
- 102100020739 Peptidyl-prolyl cis-trans isomerase FKBP4 Human genes 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 102000004631 Calcineurin Human genes 0.000 description 2
- 108010042955 Calcineurin Proteins 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 101710103508 FK506-binding protein Proteins 0.000 description 2
- 101710104425 FK506-binding protein 2 Proteins 0.000 description 2
- 101710104423 FK506-binding protein 3 Proteins 0.000 description 2
- 101710104333 FK506-binding protein 4 Proteins 0.000 description 2
- 101710104342 FK506-binding protein 5 Proteins 0.000 description 2
- 101710149710 FKBP-type 16 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710121306 FKBP-type 22 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710180800 FKBP-type peptidyl-prolyl cis-trans isomerase FkpA Proteins 0.000 description 2
- 101710104030 Long-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 101710114693 Outer membrane protein MIP Proteins 0.000 description 2
- 101710116692 Peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710111764 Peptidyl-prolyl cis-trans isomerase FKBP10 Proteins 0.000 description 2
- 101710111749 Peptidyl-prolyl cis-trans isomerase FKBP11 Proteins 0.000 description 2
- 101710111747 Peptidyl-prolyl cis-trans isomerase FKBP12 Proteins 0.000 description 2
- 101710111757 Peptidyl-prolyl cis-trans isomerase FKBP14 Proteins 0.000 description 2
- 102100027913 Peptidyl-prolyl cis-trans isomerase FKBP1A Human genes 0.000 description 2
- 101710111682 Peptidyl-prolyl cis-trans isomerase FKBP1A Proteins 0.000 description 2
- 101710111689 Peptidyl-prolyl cis-trans isomerase FKBP1B Proteins 0.000 description 2
- 101710147154 Peptidyl-prolyl cis-trans isomerase FKBP2 Proteins 0.000 description 2
- 101710147149 Peptidyl-prolyl cis-trans isomerase FKBP3 Proteins 0.000 description 2
- 101710147150 Peptidyl-prolyl cis-trans isomerase FKBP5 Proteins 0.000 description 2
- 101710147138 Peptidyl-prolyl cis-trans isomerase FKBP7 Proteins 0.000 description 2
- 101710147137 Peptidyl-prolyl cis-trans isomerase FKBP8 Proteins 0.000 description 2
- 101710147136 Peptidyl-prolyl cis-trans isomerase FKBP9 Proteins 0.000 description 2
- 101710174853 Peptidyl-prolyl cis-trans isomerase Mip Proteins 0.000 description 2
- 101710200991 Peptidyl-prolyl cis-trans isomerase, rhodopsin-specific isozyme Proteins 0.000 description 2
- 101710092145 Peptidyl-prolyl cis-trans isomerase-like 1 Proteins 0.000 description 2
- 101710092146 Peptidyl-prolyl cis-trans isomerase-like 2 Proteins 0.000 description 2
- 101710092148 Peptidyl-prolyl cis-trans isomerase-like 3 Proteins 0.000 description 2
- 101710092149 Peptidyl-prolyl cis-trans isomerase-like 4 Proteins 0.000 description 2
- 101710113444 Probable parvulin-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710090737 Probable peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710133309 Putative peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 101710124237 Short-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 description 2
- 108010006877 Tacrolimus Binding Protein 1A Proteins 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 230000001506 immunosuppresive effect Effects 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 230000001861 immunosuppressant effect Effects 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- 210000002569 neuron Anatomy 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- PLRACCBDVIHHLZ-UHFFFAOYSA-N 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1N(C)CCC(C=2C=CC=CC=2)=C1 PLRACCBDVIHHLZ-UHFFFAOYSA-N 0.000 description 1
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
- CTMKLSIFZNPXHA-UHFFFAOYSA-N 4-(2-piperidin-1-ylpiperazin-1-yl)morpholine Chemical compound C1CCCCN1C1N(N2CCOCC2)CCNC1 CTMKLSIFZNPXHA-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000021965 Glossopharyngeal Nerve disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 101001135571 Mus musculus Tyrosine-protein phosphatase non-receptor type 2 Proteins 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 208000028389 Nerve injury Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 108010020062 Peptidylprolyl Isomerase Proteins 0.000 description 1
- 102000009658 Peptidylprolyl Isomerase Human genes 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 210000005064 dopaminergic neuron Anatomy 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 210000000256 facial nerve Anatomy 0.000 description 1
- 201000005442 glossopharyngeal neuralgia Diseases 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000030214 innervation Effects 0.000 description 1
- 150000002617 leukotrienes Chemical class 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 description 1
- 230000008764 nerve damage Effects 0.000 description 1
- 230000014511 neuron projection development Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 210000003497 sciatic nerve Anatomy 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/428—Thiazoles condensed with carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Glass Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9815696.1A GB9815696D0 (en) | 1998-07-20 | 1998-07-20 | Heterocyclics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200100229B true ZA200100229B (en) | 2002-04-09 |
Family
ID=10835773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200100229A ZA200100229B (en) | 1998-07-20 | 2001-01-09 | FKBP inhibitors. |
Country Status (45)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9815696D0 (en) * | 1998-07-20 | 1998-09-16 | Pfizer Ltd | Heterocyclics |
| GB9815880D0 (en) * | 1998-07-21 | 1998-09-16 | Pfizer Ltd | Heterocycles |
| GB0008939D0 (en) | 2000-04-11 | 2000-05-31 | Glaxo Group Ltd | Process for preparing substituted benzimidazole compounds |
| AU2002241524A1 (en) | 2000-11-28 | 2002-06-11 | Wyeth | Expression analysis of FKBP nucleic acids and polypeptides useful in the diagnosis and treatment of prostate cancer |
| US7186518B2 (en) * | 2003-11-21 | 2007-03-06 | Dade Behring Inc. | Method and composition useful for determining FK 506 |
| US8354557B2 (en) | 2008-06-17 | 2013-01-15 | Concert Pharmaceuticals, Inc. | Synthesis of deuterated morpholine derivatives |
| DE102008060549A1 (de) | 2008-12-04 | 2010-06-10 | MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. | Wirkstoff-Peptid-Konstrukt zur extrazellulären Anreicherung |
| TWI534142B (zh) | 2011-03-15 | 2016-05-21 | 大正製藥股份有限公司 | Azole derivatives |
| EP2705856A1 (en) | 2012-09-07 | 2014-03-12 | Deutsches Zentrum für Neurodegenerative Erkrankungen e.V. | Compounds for the treatment of neurodegenerative disorders |
| CN106138044B (zh) * | 2016-07-15 | 2017-05-03 | 鲁俊东 | 一种治疗腰椎间盘突出症的药物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI91859C (fi) * | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| FR2696176B1 (fr) * | 1992-09-28 | 1994-11-10 | Synthelabo | Dérivés de pipéridine, leur préparation et leur application en thérapeutique. |
| CO4520280A1 (es) * | 1993-10-26 | 1997-10-15 | Boehringer Ingelheim Pharma | Derivados de pirrolidina, inhibidores de la bioscientesis de leucotrienos |
| US5801187A (en) * | 1996-09-25 | 1998-09-01 | Gpi-Nil Holdings, Inc. | Heterocyclic esters and amides |
| GB9700597D0 (en) * | 1997-01-14 | 1997-03-05 | Sandoz Pharma Uk | Organic compounds |
| US5721256A (en) * | 1997-02-12 | 1998-02-24 | Gpi Nil Holdings, Inc. | Method of using neurotrophic sulfonamide compounds |
| GB9815696D0 (en) * | 1998-07-20 | 1998-09-16 | Pfizer Ltd | Heterocyclics |
| GB9815880D0 (en) * | 1998-07-21 | 1998-09-16 | Pfizer Ltd | Heterocycles |
| US6495549B1 (en) * | 1999-07-15 | 2002-12-17 | Pfizer Inc | FKBP inhibitors |
-
1998
- 1998-07-20 GB GBGB9815696.1A patent/GB9815696D0/en not_active Ceased
-
1999
- 1999-01-07 UA UA2001010434A patent/UA60368C2/uk unknown
- 1999-06-30 HN HN1999000101A patent/HN1999000101A/es unknown
- 1999-07-01 WO PCT/IB1999/001227 patent/WO2000005231A1/en not_active Application Discontinuation
- 1999-07-01 KR KR1020017000834A patent/KR20010083130A/ko not_active Application Discontinuation
- 1999-07-01 ID IDW20010154A patent/ID27022A/id unknown
- 1999-07-01 OA OA1200100024A patent/OA11586A/en unknown
- 1999-07-01 EP EP99926683A patent/EP1098894B1/en not_active Expired - Lifetime
- 1999-07-01 TR TR2001/00133T patent/TR200100133T2/xx unknown
- 1999-07-01 JP JP2000561187A patent/JP3545341B2/ja not_active Expired - Fee Related
- 1999-07-01 SK SK70-2001A patent/SK702001A3/sk unknown
- 1999-07-01 PT PT99926683T patent/PT1098894E/pt unknown
- 1999-07-01 DE DE69903319T patent/DE69903319T2/de not_active Expired - Fee Related
- 1999-07-01 EE EEP200100043A patent/EE200100043A/xx unknown
- 1999-07-01 ES ES99926683T patent/ES2183567T3/es not_active Expired - Lifetime
- 1999-07-01 IL IL14024399A patent/IL140243A0/xx unknown
- 1999-07-01 CN CN99810385A patent/CN1315951A/zh active Pending
- 1999-07-01 YU YU83100A patent/YU83100A/sh unknown
- 1999-07-01 NZ NZ508839A patent/NZ508839A/xx unknown
- 1999-07-01 PL PL99345705A patent/PL345705A1/xx not_active Application Discontinuation
- 1999-07-01 AP APAP/P/2001/002045A patent/AP2001002045A0/en unknown
- 1999-07-01 CZ CZ2001224A patent/CZ2001224A3/cs unknown
- 1999-07-01 BR BR9912307-0A patent/BR9912307A/pt not_active Application Discontinuation
- 1999-07-01 AU AU43855/99A patent/AU756769B2/en not_active Ceased
- 1999-07-01 HU HU0103020A patent/HUP0103020A3/hu unknown
- 1999-07-01 CA CA002338276A patent/CA2338276C/en not_active Expired - Fee Related
- 1999-07-01 AT AT99926683T patent/ATE225346T1/de not_active IP Right Cessation
- 1999-07-01 DK DK99926683T patent/DK1098894T3/da active
- 1999-07-01 SI SI9930120T patent/SI1098894T1/xx unknown
- 1999-07-01 EA EA200100051A patent/EA200100051A1/ru unknown
- 1999-07-12 PA PA19998477601A patent/PA8477601A1/es unknown
- 1999-07-15 US US09/354,193 patent/US6166011A/en not_active Expired - Fee Related
- 1999-07-16 PE PE1999000722A patent/PE20000867A1/es not_active Application Discontinuation
- 1999-07-19 DZ DZ990148A patent/DZ2848A1/xx active
- 1999-07-19 CO CO99045678A patent/CO5080761A1/es unknown
- 1999-07-19 AR ARP990103543A patent/AR016501A1/es not_active Application Discontinuation
- 1999-07-19 MA MA25689A patent/MA26661A1/fr unknown
- 1999-07-19 TN TNTNSN99146A patent/TNSN99146A1/fr unknown
- 1999-07-19 GT GT199900113A patent/GT199900113A/es unknown
-
2000
- 2000-12-29 IS IS5799A patent/IS5799A/is unknown
-
2001
- 2001-01-09 ZA ZA200100229A patent/ZA200100229B/en unknown
- 2001-01-18 NO NO20010299A patent/NO20010299L/no not_active Application Discontinuation
- 2001-01-19 HR HR20010053A patent/HRP20010053A2/hr not_active Application Discontinuation
- 2001-02-14 BG BG105249A patent/BG105249A/xx unknown
-
2002
- 2002-03-26 HK HK02102302.7A patent/HK1040706A1/zh unknown
-
2003
- 2003-04-01 US US10/404,524 patent/US20040058905A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107207487B (zh) | 用于提高cftr活性的化合物、组合物和方法 | |
| EP2981536B1 (en) | N-phenyl-carboxamide derivatives and the use thereof as medicaments for the treatment of hepatitis b | |
| EP3642196B1 (en) | Substituted cyanopyrrolidines with activity as dub inhibitors | |
| US6544987B2 (en) | Compounds, compositions, and methods for stimulating neuronal growth and elongation | |
| JP2019521082A (ja) | Ｌｓｄ１／ｈｄａｃ二重阻害剤としてのシクロプロピル−アミド化合物 | |
| WO2017030814A1 (en) | Compounds and methods for the targeted degradation of bromodomain-containing proteins | |
| CN108283000A (zh) | γ-羟基丁酸的前药及其组合物和用途 | |
| CN103221392A (zh) | 桥联螺[2.4]庚酯衍生物 | |
| ZA200100229B (en) | FKBP inhibitors. | |
| JP2009167215A (ja) | 新規ジアリールアルケン誘導体及び新規ジアリールアルカン誘導体 | |
| EP3037412B1 (en) | Indole amide compound as inhibitor of necrosis | |
| WO2009106967A1 (fr) | Nouveaux derives 7-substitues de 3-carboxy-oxadiazino-quinolones, leur preparation et leur application comme anti-bacteriens | |
| EP1661898A1 (en) | Bicyclic piperazine compound and use thereof | |
| TWI570119B (zh) | （２ｓ）－３－［（３ｓ，４ｓ）－３－［（１ｒ）－１－羥乙基］－４－（４－甲氧基－３－｛［１－（５－甲基吡啶－２－基）吖丁啶－３－基］氧基｝苯基）－３－甲基吡咯啶－１－基］－３－氧代丙烷－１，２－二醇結晶型及其用途 | |
| EP1778637B1 (en) | FKBP-binding composition and pharmaceutical use thereof | |
| US6495549B1 (en) | FKBP inhibitors | |
| HRP20010118A2 (en) | Compounds, compositions, and methods for stimulating neuronal growth and elongation | |
| TW202204341A (zh) | Ｎ－雜芳基烷基－２－（雜環基及雜環基甲基）乙醯胺衍生物 | |
| US20020042377A1 (en) | Rotamase enzyme activity inhibitors | |
| Karjalainen | Substrate Controlled Synthesis of 1, 2-Amino Alcohols | |
| EA038135B1 (ru) | Замещенные пирролизины и их применение | |
| 宮崎理樹 | Study on p53-MDM2 Interaction Inhibitors as a Novel Anticancer Agent | |
| JP2005306839A (ja) | 二環性ピペラジン化合物およびその用途 | |
| MXPA06004271A (en) | Derivatives of n-[heteroaryl(piperidine-2-yl)methyl]benzamide, preparation method thereof and application of same in therapeutics |