ZA200100320B - Compounds, compositions and methods for stimulating neuronal growth and elongation. - Google Patents
Compounds, compositions and methods for stimulating neuronal growth and elongation. Download PDFInfo
- Publication number
- ZA200100320B ZA200100320B ZA200100320A ZA200100320A ZA200100320B ZA 200100320 B ZA200100320 B ZA 200100320B ZA 200100320 A ZA200100320 A ZA 200100320A ZA 200100320 A ZA200100320 A ZA 200100320A ZA 200100320 B ZA200100320 B ZA 200100320B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- alkyl
- compound
- substituted
- unsubstituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 86
- 238000000034 method Methods 0.000 title claims description 22
- 239000000203 mixture Substances 0.000 title description 6
- 230000007514 neuronal growth Effects 0.000 title description 5
- 230000004936 stimulating effect Effects 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- 229910052799 carbon Inorganic materials 0.000 claims description 98
- 125000001424 substituent group Chemical group 0.000 claims description 61
- 125000003342 alkenyl group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- -1 benzyloxy, phenoxy, amino Chemical group 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 101710103508 FK506-binding protein Proteins 0.000 claims description 18
- 101710104425 FK506-binding protein 2 Proteins 0.000 claims description 18
- 101710104423 FK506-binding protein 3 Proteins 0.000 claims description 18
- 101710104333 FK506-binding protein 4 Proteins 0.000 claims description 18
- 101710104342 FK506-binding protein 5 Proteins 0.000 claims description 18
- 101710149710 FKBP-type 16 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710121306 FKBP-type 22 kDa peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710180800 FKBP-type peptidyl-prolyl cis-trans isomerase FkpA Proteins 0.000 claims description 18
- 101710104030 Long-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710114693 Outer membrane protein MIP Proteins 0.000 claims description 18
- 101710116692 Peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710111764 Peptidyl-prolyl cis-trans isomerase FKBP10 Proteins 0.000 claims description 18
- 101710111749 Peptidyl-prolyl cis-trans isomerase FKBP11 Proteins 0.000 claims description 18
- 101710111747 Peptidyl-prolyl cis-trans isomerase FKBP12 Proteins 0.000 claims description 18
- 101710111757 Peptidyl-prolyl cis-trans isomerase FKBP14 Proteins 0.000 claims description 18
- 101710111682 Peptidyl-prolyl cis-trans isomerase FKBP1A Proteins 0.000 claims description 18
- 101710111689 Peptidyl-prolyl cis-trans isomerase FKBP1B Proteins 0.000 claims description 18
- 101710147154 Peptidyl-prolyl cis-trans isomerase FKBP2 Proteins 0.000 claims description 18
- 101710147149 Peptidyl-prolyl cis-trans isomerase FKBP3 Proteins 0.000 claims description 18
- 101710147152 Peptidyl-prolyl cis-trans isomerase FKBP4 Proteins 0.000 claims description 18
- 101710147150 Peptidyl-prolyl cis-trans isomerase FKBP5 Proteins 0.000 claims description 18
- 101710147138 Peptidyl-prolyl cis-trans isomerase FKBP7 Proteins 0.000 claims description 18
- 101710147137 Peptidyl-prolyl cis-trans isomerase FKBP8 Proteins 0.000 claims description 18
- 101710147136 Peptidyl-prolyl cis-trans isomerase FKBP9 Proteins 0.000 claims description 18
- 101710174853 Peptidyl-prolyl cis-trans isomerase Mip Proteins 0.000 claims description 18
- 101710200991 Peptidyl-prolyl cis-trans isomerase, rhodopsin-specific isozyme Proteins 0.000 claims description 18
- 101710092145 Peptidyl-prolyl cis-trans isomerase-like 1 Proteins 0.000 claims description 18
- 101710092146 Peptidyl-prolyl cis-trans isomerase-like 2 Proteins 0.000 claims description 18
- 101710092148 Peptidyl-prolyl cis-trans isomerase-like 3 Proteins 0.000 claims description 18
- 101710092149 Peptidyl-prolyl cis-trans isomerase-like 4 Proteins 0.000 claims description 18
- 101710113444 Probable parvulin-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710090737 Probable peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710133309 Putative peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- 101710124237 Short-type peptidyl-prolyl cis-trans isomerase Proteins 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 108010025020 Nerve Growth Factor Proteins 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 6
- 239000002207 metabolite Substances 0.000 claims description 6
- 239000000651 prodrug Substances 0.000 claims description 6
- 229940002612 prodrug Drugs 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 102000015336 Nerve Growth Factor Human genes 0.000 claims description 5
- 102000007072 Nerve Growth Factors Human genes 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 229940053128 nerve growth factor Drugs 0.000 claims description 5
- 239000003900 neurotrophic factor Substances 0.000 claims description 5
- 108090000099 Neurotrophin-4 Proteins 0.000 claims description 4
- 102100033857 Neurotrophin-4 Human genes 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 239000003102 growth factor Substances 0.000 claims description 4
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 102100037597 Brain-derived neurotrophic factor Human genes 0.000 claims description 2
- 108090000715 Brain-derived neurotrophic factor Proteins 0.000 claims description 2
- 102000003971 Fibroblast Growth Factor 1 Human genes 0.000 claims description 2
- 108090000386 Fibroblast Growth Factor 1 Proteins 0.000 claims description 2
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 claims description 2
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 claims description 2
- 108090001061 Insulin Proteins 0.000 claims description 2
- 102000004877 Insulin Human genes 0.000 claims description 2
- 108090000742 Neurotrophin 3 Proteins 0.000 claims description 2
- 102000004230 Neurotrophin 3 Human genes 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229940077737 brain-derived neurotrophic factor Drugs 0.000 claims description 2
- 230000001886 ciliary effect Effects 0.000 claims description 2
- 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 229940125396 insulin Drugs 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229940032018 neurotrophin 3 Drugs 0.000 claims description 2
- 229940097998 neurotrophin 4 Drugs 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
- 235000015250 liver sausages Nutrition 0.000 claims 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- 229910052754 neon Inorganic materials 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- 102000034615 Glial cell line-derived neurotrophic factor Human genes 0.000 claims 1
- 108091010837 Glial cell line-derived neurotrophic factor Proteins 0.000 claims 1
- 101001072091 Homo sapiens ProSAAS Proteins 0.000 claims 1
- 102100038809 Peptidyl-prolyl cis-trans isomerase FKBP9 Human genes 0.000 claims 1
- 102100036366 ProSAAS Human genes 0.000 claims 1
- 229910019567 Re Re Inorganic materials 0.000 claims 1
- 239000008186 active pharmaceutical agent Substances 0.000 claims 1
- HKIOYBQGHSTUDB-UHFFFAOYSA-N folpet Chemical group C1=CC=C2C(=O)N(SC(Cl)(Cl)Cl)C(=O)C2=C1 HKIOYBQGHSTUDB-UHFFFAOYSA-N 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 102100020739 Peptidyl-prolyl cis-trans isomerase FKBP4 Human genes 0.000 description 17
- 108010027179 Tacrolimus Binding Proteins Proteins 0.000 description 14
- 102000018679 Tacrolimus Binding Proteins Human genes 0.000 description 14
- 230000000694 effects Effects 0.000 description 11
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 9
- 229960001967 tacrolimus Drugs 0.000 description 9
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 9
- 108010006877 Tacrolimus Binding Protein 1A Proteins 0.000 description 8
- 230000014511 neuron projection development Effects 0.000 description 8
- 102100027913 Peptidyl-prolyl cis-trans isomerase FKBP1A Human genes 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 208000006011 Stroke Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000001537 neural effect Effects 0.000 description 6
- 102000004631 Calcineurin Human genes 0.000 description 5
- 108010042955 Calcineurin Proteins 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 208000014674 injury Diseases 0.000 description 5
- 230000000508 neurotrophic effect Effects 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000000521 Immunophilins Human genes 0.000 description 4
- 108010016648 Immunophilins Proteins 0.000 description 4
- 208000028389 Nerve injury Diseases 0.000 description 4
- 102000009658 Peptidylprolyl Isomerase Human genes 0.000 description 4
- 108010020062 Peptidylprolyl Isomerase Proteins 0.000 description 4
- 230000008764 nerve damage Effects 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- 238000011069 regeneration method Methods 0.000 description 4
- 102000019027 Ryanodine Receptor Calcium Release Channel Human genes 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 230000001506 immunosuppresive effect Effects 0.000 description 3
- 239000003018 immunosuppressive agent Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 230000008439 repair process Effects 0.000 description 3
- 108091052345 ryanodine receptor (TC 1.A.3.1) family Proteins 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- 208000006373 Bell palsy Diseases 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 2
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 2
- 208000036826 VIIth nerve paralysis Diseases 0.000 description 2
- 208000027418 Wounds and injury Diseases 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000006931 brain damage Effects 0.000 description 2
- 231100000874 brain damage Toxicity 0.000 description 2
- 208000029028 brain injury Diseases 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 230000002596 correlated effect Effects 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 229960003444 immunosuppressant agent Drugs 0.000 description 2
- 230000001861 immunosuppressant effect Effects 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 208000005264 motor neuron disease Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 201000006938 muscular dystrophy Diseases 0.000 description 2
- 206010028417 myasthenia gravis Diseases 0.000 description 2
- 210000000653 nervous system Anatomy 0.000 description 2
- 208000004296 neuralgia Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
- 230000009689 neuronal regeneration Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 210000000578 peripheral nerve Anatomy 0.000 description 2
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 229960002930 sirolimus Drugs 0.000 description 2
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 102000003922 Calcium Channels Human genes 0.000 description 1
- 108090000312 Calcium Channels Proteins 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 108010036949 Cyclosporine Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010062016 Immunosuppression Diseases 0.000 description 1
- 102000007640 Inositol 1,4,5-Trisphosphate Receptors Human genes 0.000 description 1
- 108010032354 Inositol 1,4,5-Trisphosphate Receptors Proteins 0.000 description 1
- 108010002350 Interleukin-2 Proteins 0.000 description 1
- 230000006052 T cell proliferation Effects 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 102000040945 Transcription factor Human genes 0.000 description 1
- 108091023040 Transcription factor Proteins 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000003190 augmentative effect Effects 0.000 description 1
- 210000003050 axon Anatomy 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 230000003185 calcium uptake Effects 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000003915 cell function Effects 0.000 description 1
- 229960001265 ciclosporin Drugs 0.000 description 1
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 1
- 238000012875 competitive assay Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000030609 dephosphorylation Effects 0.000 description 1
- 238000006209 dephosphorylation reaction Methods 0.000 description 1
- RQYGKZGKXDOUEO-LFZNUXCKSA-N dihydro-fk-506 Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C/C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CCC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 RQYGKZGKXDOUEO-LFZNUXCKSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000002241 neurite Anatomy 0.000 description 1
- 230000007971 neurological deficit Effects 0.000 description 1
- 230000003961 neuronal insult Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 208000028591 pheochromocytoma Diseases 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005306 thianaphthenyl group Chemical group 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C07D471/02—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 two hetero rings
- C07D471/08—Bridged systems
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US9329998P | 1998-07-17 | 1998-07-17 | |
US13288499P | 1999-05-06 | 1999-05-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200100320B true ZA200100320B (en) | 2002-07-11 |
Family
ID=26787372
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200100320A ZA200100320B (en) | 1998-07-17 | 2001-01-11 | Compounds, compositions and methods for stimulating neuronal growth and elongation. |
Country Status (35)
Country | Link |
---|---|
US (1) | US6630472B1 (xx) |
EP (1) | EP1098897B1 (xx) |
JP (1) | JP2002520413A (xx) |
KR (1) | KR20010071920A (xx) |
CN (1) | CN1318067A (xx) |
AP (1) | AP2001002052A0 (xx) |
AT (1) | ATE268772T1 (xx) |
AU (1) | AU756912B2 (xx) |
BG (1) | BG105268A (xx) |
BR (1) | BR9912423A (xx) |
CA (1) | CA2337377A1 (xx) |
DE (1) | DE69917907T2 (xx) |
DK (1) | DK1098897T3 (xx) |
EA (1) | EA200100149A1 (xx) |
EE (1) | EE200100032A (xx) |
ES (1) | ES2226409T3 (xx) |
GE (1) | GEP20043368B (xx) |
HR (1) | HRP20010118A2 (xx) |
HU (1) | HUP0200637A3 (xx) |
ID (1) | ID27428A (xx) |
IL (1) | IL140676A0 (xx) |
IS (1) | IS5805A (xx) |
LT (1) | LT4850B (xx) |
LV (1) | LV12665B (xx) |
NO (1) | NO20010191L (xx) |
NZ (1) | NZ509211A (xx) |
OA (1) | OA11581A (xx) |
PL (1) | PL345598A1 (xx) |
PT (1) | PT1098897E (xx) |
SI (1) | SI20638A (xx) |
SK (1) | SK462001A3 (xx) |
TR (1) | TR200100122T2 (xx) |
WO (1) | WO2000004020A1 (xx) |
YU (1) | YU2901A (xx) |
ZA (1) | ZA200100320B (xx) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6818643B1 (en) * | 1999-12-08 | 2004-11-16 | Bristol-Myers Squibb Company | Neurotrophic bicyclic diamides |
BR0210060A (pt) * | 2001-05-10 | 2004-08-17 | Agouron Pharma | Ligandos de fkbp de heterobiciclos |
EP3097103B1 (en) * | 2014-01-24 | 2017-11-15 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften | Diazabicyclo[4.3.1]decane derivatives for treatment of psychiatric disorders |
EP2899192A1 (en) * | 2014-01-24 | 2015-07-29 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Diazabicyclo[4.3.1]decane derivatives for treatment of psychiatric disorders |
Family Cites Families (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4894366A (en) | 1984-12-03 | 1990-01-16 | Fujisawa Pharmaceutical Company, Ltd. | Tricyclo compounds, a process for their production and a pharmaceutical composition containing the same |
US5196352A (en) | 1989-01-19 | 1993-03-23 | Merck & Co., Inc. | New FK-506 cytosolic binding protein |
US5109112A (en) | 1989-01-19 | 1992-04-28 | Merck & Co., Inc. | FK-506 cytosolic binding protein |
US5192773A (en) | 1990-07-02 | 1993-03-09 | Vertex Pharmaceuticals, Inc. | Immunosuppressive compounds |
US5187166A (en) * | 1990-07-31 | 1993-02-16 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives and their use as antiemetics |
US5256656A (en) * | 1990-07-31 | 1993-10-26 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives |
CA2068062A1 (en) | 1991-05-07 | 1992-11-08 | Stephen A. Parent | Yeast mutants |
US5362629A (en) | 1991-08-05 | 1994-11-08 | President And Fellows Of Harvard College | Detection of immunosuppressants |
US5344831A (en) * | 1992-01-31 | 1994-09-06 | Nisshin Flour Milling Co., Ltd. | Diazabicyclo derivatives |
DE4219973A1 (de) | 1992-06-19 | 1993-12-23 | Basf Ag | N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung |
US5318895A (en) | 1992-10-05 | 1994-06-07 | Merck & Co., Inc. | Aspergillus niger mutants |
US5798355A (en) | 1995-06-07 | 1998-08-25 | Gpi Nil Holdings, Inc. | Inhibitors of rotamase enzyme activity |
JP3235913B2 (ja) * | 1993-07-30 | 2001-12-04 | エーザイ株式会社 | アミノ安息香酸誘導体 |
US5612350A (en) | 1993-11-30 | 1997-03-18 | Abbott Laboratories | Macrocyclic immunomodulators with novel cyclohexyl ring replacements |
DE4341402A1 (de) | 1993-12-04 | 1995-06-08 | Basf Ag | N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung |
US5457182A (en) | 1994-02-15 | 1995-10-10 | Merck & Co., Inc. | FK-506 cytosolic binding protein, FKBP12.6 |
US5622866A (en) | 1994-06-23 | 1997-04-22 | Merck & Co., Inc. | Expression cassettes useful in construction of integrative and replicative expression vectors for Streptomyces |
US5614547A (en) | 1995-06-07 | 1997-03-25 | Guilford Pharmaceuticals Inc. | Small molecule inhibitors of rotamase enzyme |
US5859031A (en) | 1995-06-07 | 1999-01-12 | Gpi Nil Holdings, Inc. | Small molecule inhibitors of rotamase enzyme activity |
US5696135A (en) | 1995-06-07 | 1997-12-09 | Gpi Nil Holdings, Inc. | Inhibitors of rotamase enzyme activity effective at stimulating neuronal growth |
US6037370A (en) | 1995-06-08 | 2000-03-14 | Vertex Pharmaceuticals Incorporated | Methods and compositions for stimulating neurite growth |
US5801197A (en) * | 1995-10-31 | 1998-09-01 | Gpi Nil Holdings, Inc. | Rotamase enzyme activity inhibitors |
US5801187A (en) | 1996-09-25 | 1998-09-01 | Gpi-Nil Holdings, Inc. | Heterocyclic esters and amides |
US5786378A (en) * | 1996-09-25 | 1998-07-28 | Gpi Nil Holdings, Inc. | Heterocyclic thioesters |
US5840736A (en) | 1996-11-13 | 1998-11-24 | Vertex Pharmaceuticals Incorporated | Methods and compositions for stimulating neurite growth |
US5780484A (en) | 1996-11-13 | 1998-07-14 | Vertex Pharmaceuticals Incorporated | Methods for stimulating neurite growth with piperidine compounds |
US5811434A (en) | 1996-11-13 | 1998-09-22 | Vertex Pharmacueticals Incorporated | Methods and compositions for stimulating neurite growth |
AR010744A1 (es) | 1996-12-09 | 2000-07-12 | Guildford Pharmaceuticals Inc | Inhibidores polipropilos de ciclofilina |
US5874449A (en) | 1996-12-31 | 1999-02-23 | Gpi Nil Holdings, Inc. | N-linked sulfonamides of heterocyclic thioesters |
US5935989A (en) | 1996-12-31 | 1999-08-10 | Gpi Nil Holdings Inc. | N-linked ureas and carbamates of heterocyclic thioesters |
US5721256A (en) | 1997-02-12 | 1998-02-24 | Gpi Nil Holdings, Inc. | Method of using neurotrophic sulfonamide compounds |
ZA98825B (en) | 1997-02-27 | 1998-10-19 | Guilford Pharm Inc | Method of using neurotrophic carbamates and ureas |
US5846979A (en) | 1997-02-28 | 1998-12-08 | Gpi Nil Holdings, Inc. | N-oxides of heterocyclic esters, amides, thioesters, and ketones |
-
1999
- 1999-07-15 EP EP99934043A patent/EP1098897B1/en not_active Expired - Lifetime
- 1999-07-15 KR KR1020017000654A patent/KR20010071920A/ko not_active Application Discontinuation
- 1999-07-15 CN CN99810848A patent/CN1318067A/zh active Pending
- 1999-07-15 ES ES99934043T patent/ES2226409T3/es not_active Expired - Lifetime
- 1999-07-15 ID IDW20010130A patent/ID27428A/id unknown
- 1999-07-15 GE GE4273A patent/GEP20043368B/en unknown
- 1999-07-15 BR BR9912423-8A patent/BR9912423A/pt not_active Application Discontinuation
- 1999-07-15 PT PT99934043T patent/PT1098897E/pt unknown
- 1999-07-15 YU YU2901A patent/YU2901A/sh unknown
- 1999-07-15 NZ NZ509211A patent/NZ509211A/xx unknown
- 1999-07-15 SK SK46-2001A patent/SK462001A3/sk unknown
- 1999-07-15 AT AT99934043T patent/ATE268772T1/de not_active IP Right Cessation
- 1999-07-15 AU AU49963/99A patent/AU756912B2/en not_active Ceased
- 1999-07-15 JP JP2000560126A patent/JP2002520413A/ja not_active Withdrawn
- 1999-07-15 PL PL99345598A patent/PL345598A1/xx not_active Application Discontinuation
- 1999-07-15 TR TR2001/00122T patent/TR200100122T2/xx unknown
- 1999-07-15 HU HU0200637A patent/HUP0200637A3/hu unknown
- 1999-07-15 DE DE69917907T patent/DE69917907T2/de not_active Expired - Fee Related
- 1999-07-15 EE EEP200100032A patent/EE200100032A/xx unknown
- 1999-07-15 DK DK99934043T patent/DK1098897T3/da active
- 1999-07-15 SI SI9920067A patent/SI20638A/sl not_active IP Right Cessation
- 1999-07-15 CA CA002337377A patent/CA2337377A1/en not_active Abandoned
- 1999-07-15 AP APAP/P/2001/002052A patent/AP2001002052A0/en unknown
- 1999-07-15 IL IL14067699A patent/IL140676A0/xx unknown
- 1999-07-15 EA EA200100149A patent/EA200100149A1/ru unknown
- 1999-07-15 OA OA1200100015A patent/OA11581A/en unknown
- 1999-07-15 WO PCT/US1999/015965 patent/WO2000004020A1/en not_active Application Discontinuation
- 1999-07-16 US US09/356,240 patent/US6630472B1/en not_active Expired - Fee Related
-
2001
- 2001-01-11 ZA ZA200100320A patent/ZA200100320B/en unknown
- 2001-01-12 IS IS5805A patent/IS5805A/is unknown
- 2001-01-12 NO NO20010191A patent/NO20010191L/no not_active Application Discontinuation
- 2001-02-15 LT LT2001012A patent/LT4850B/lt not_active IP Right Cessation
- 2001-02-16 HR HR20010118A patent/HRP20010118A2/hr not_active Application Discontinuation
- 2001-02-16 BG BG105268A patent/BG105268A/xx unknown
- 2001-03-13 LV LV010023A patent/LV12665B/lv unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR0167101B1 (ko) | [r-(r*,r*)]-2-(4-플루오로페닐)-베타, 델타-디히드록시-5-(1-메틸에틸)-3-페닐-4-[(페닐아미노)카르보닐]-1h-피롤-1-헵탄산, 그의 락톤형 및 염류 | |
RU2041211C1 (ru) | Конденсированные 5-членные гетероциклы или их соли, проявляющие активность по торможению агрегации | |
US5177080A (en) | Substituted pyridyl-dihydroxy-heptenoic acid and its salts | |
US5670534A (en) | Distamycin a derivatives as anti-malarial agents | |
EA027828B1 (ru) | Противовирусные соединения | |
KR20000048589A (ko) | 헤테로고리형 에스테르 및 아미드 | |
US11840514B2 (en) | Catalysts and methods for enantioselective conjugate addition of amines to unsaturated electrophiles | |
JPS5976086A (ja) | プテリジン化合物 | |
HUT71353A (en) | 4-[4'-piperidinyl or 3'pirrolidinyl] substituted imidazoles as h3-receptor antagonists and therapeutic uses thereof | |
HU210822A9 (en) | Pyrimidine-4,6-dicarboxylic acid diamides, processes for the use thereof, and pharmaceuticals based on these compounds | |
US6365585B1 (en) | Phosphodiesterase IV-inhibiting diazepinoindoles | |
Lv et al. | hERG optimizations of IMB1603, discovery of alternative benzothiazinones as new antitubercular agents | |
JP5220601B2 (ja) | コリスマイシンおよびその誘導体の、酸化ストレス抑制剤としての使用 | |
ZA200100320B (en) | Compounds, compositions and methods for stimulating neuronal growth and elongation. | |
US4985433A (en) | 2-amino-7-(pyridinylmethyl)-3H,5H-pyrrolo[3,2-d]pyrimidin-4-ones and pharmaceutical uses and compositions containing the same | |
SK282766B6 (sk) | Diazepinoindoly ako inhibítory fosfodiesterázy IV, ich použitie ako liečiv a farmaceutické kompozície s ich obsahom | |
UA81640C2 (ru) | Противомикобактериальные соединения, способ их получения, фармацевтическая композиция на их основе | |
DD294260A5 (de) | Verfahren zur herstellung von substituierten pyrrolverbindungen | |
MXPA05012900A (es) | Derivados de pirrol sustituidos. | |
Antonucci et al. | Characterization of the antiviral activity of highly substituted pyrroles: a novel class of non-nucleoside HIV-1 reverse transcriptase inhibitor | |
WO2005053702A2 (en) | Anti-inflammatory agents | |
JPH01193264A (ja) | 精神分裂病の治療に有効な1−((5−((4−置換−1−ピペラジニル)メチル)−ピロール−2−イル又はフラン−2−イル)メチル−2−ピペリジノン類 | |
JP2007537242A (ja) | 抗マイコバクテリア医薬組成物 | |
US5714500A (en) | 2-phenyl- and 2-thienyl-(2)-piperidine derivatives having neuroprotective properties | |
AU2002250997B2 (en) | Use of thiolutin dioxide and its derivatives in the manufacture of a medicament for the treatment of CNS disorders and a process for the preparation thereof |