MXPA01001642A

MXPA01001642A - Derivados de acido pipecolico para trastornos de la vision y de la memoria.

Derivados de acido pipecolico para trastornos de la vision y de la memoria.

Info

Publication number: MXPA01001642A
Authority: MX; Mexico
Prior art keywords: piperidinecarboxylate; dimethyl; oxopentanoyl; oxoacetyl; oxo
Prior art date: 1998-08-14

Application number

MXPA01001642A

Other languages

English (en)

Spanish (es)

Inventor

Gregory S Hamilton

Original Assignee

Guilford Pharm Inc

Priority date

1998-08-14

Filing date

1999-08-12

Publication date

2002-06-04

1999-08-12 Application filed by Guilford Pharm Inc filed Critical Guilford Pharm Inc

2002-06-04 Publication of MXPA01001642A publication Critical patent/MXPA01001642A/es

Links

HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical class [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 title claims abstract description 40
208000029257 vision disease Diseases 0.000 title claims abstract description 22
230000004438 eyesight Effects 0.000 title claims description 37
208000026139 Memory disease Diseases 0.000 title 1
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 32
206010027175 memory impairment Diseases 0.000 claims abstract description 11
230000007334 memory performance Effects 0.000 claims abstract description 9
230000004377 improving vision Effects 0.000 claims abstract description 7
-1 3- cyclohexylpropyl pyridinecarboxylate Chemical compound 0.000 claims description 102
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 101
238000011282 treatment Methods 0.000 claims description 89
210000001328 optic nerve Anatomy 0.000 claims description 88
150000001875 compounds Chemical class 0.000 claims description 82
208000035475 disorder Diseases 0.000 claims description 69
230000007850 degeneration Effects 0.000 claims description 47
210000001508 eye Anatomy 0.000 claims description 43
241001465754 Metazoa Species 0.000 claims description 38
201000010099 disease Diseases 0.000 claims description 32
230000006378 damage Effects 0.000 claims description 30
230000004393 visual impairment Effects 0.000 claims description 27
108010027179 Tacrolimus Binding Proteins Proteins 0.000 claims description 22
102000018679 Tacrolimus Binding Proteins Human genes 0.000 claims description 22
208000027418 Wounds and injury Diseases 0.000 claims description 22
210000001525 retina Anatomy 0.000 claims description 21
208000014674 injury Diseases 0.000 claims description 20
208000030533 eye disease Diseases 0.000 claims description 19
230000015654 memory Effects 0.000 claims description 17
239000003018 immunosuppressive agent Substances 0.000 claims description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
206010047571 Visual impairment Diseases 0.000 claims description 14
229960003444 immunosuppressant agent Drugs 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
GWXADOKFGBKLOD-UHFFFAOYSA-N 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylic acid Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCCC1C(O)=O GWXADOKFGBKLOD-UHFFFAOYSA-N 0.000 claims description 11
208000010412 Glaucoma Diseases 0.000 claims description 11
210000004087 cornea Anatomy 0.000 claims description 11
230000001404 mediated effect Effects 0.000 claims description 11
108010025020 Nerve Growth Factor Proteins 0.000 claims description 10
210000000744 eyelid Anatomy 0.000 claims description 10
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 claims description 10
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 claims description 10
229960002930 sirolimus Drugs 0.000 claims description 10
238000001356 surgical procedure Methods 0.000 claims description 10
208000024891 symptom Diseases 0.000 claims description 10
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
102100027913 Peptidyl-prolyl cis-trans isomerase FKBP1A Human genes 0.000 claims description 9
108010006877 Tacrolimus Binding Protein 1A Proteins 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
208000015122 neurodegenerative disease Diseases 0.000 claims description 9
208000032843 Hemorrhage Diseases 0.000 claims description 8
102000007072 Nerve Growth Factors Human genes 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
210000000795 conjunctiva Anatomy 0.000 claims description 8
239000003102 growth factor Substances 0.000 claims description 8
208000002780 macular degeneration Diseases 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
102000000521 Immunophilins Human genes 0.000 claims description 7
108010016648 Immunophilins Proteins 0.000 claims description 7
206010029113 Neovascularisation Diseases 0.000 claims description 7
230000001861 immunosuppressant effect Effects 0.000 claims description 7
239000003900 neurotrophic factor Substances 0.000 claims description 7
208000020564 Eye injury Diseases 0.000 claims description 6
230000001363 autoimmune Effects 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
230000014511 neuron projection development Effects 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
230000004400 visual pathway Effects 0.000 claims description 6
210000000239 visual pathway Anatomy 0.000 claims description 6
239000003963 antioxidant agent Substances 0.000 claims description 5
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230000006872 improvement Effects 0.000 claims description 5
230000004410 intraocular pressure Effects 0.000 claims description 4
230000004792 oxidative damage Effects 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
210000001519 tissue Anatomy 0.000 claims description 4
KKDVLTPMKNJRHI-UHFFFAOYSA-N 1-(3,3-dimethylbutanoyl)piperidine-2-carboxylic acid Chemical compound CC(C)(C)CC(=O)N1CCCCC1C(O)=O KKDVLTPMKNJRHI-UHFFFAOYSA-N 0.000 claims description 3
206010052428 Wound Diseases 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims description 3
210000004561 lacrimal apparatus Anatomy 0.000 claims description 3
238000002483 medication Methods 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000003357 wound healing promoting agent Substances 0.000 claims description 3
WTWAHPUUXVQCGB-UHFFFAOYSA-N 1-benzylsulfonylpiperidine-2-carboxylic acid Chemical compound OC(=O)C1CCCCN1S(=O)(=O)CC1=CC=CC=C1 WTWAHPUUXVQCGB-UHFFFAOYSA-N 0.000 claims description 2
TWIPMAAXAROIGN-UHFFFAOYSA-N ethyl 1-(3-methyl-2-oxobutanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)C(C)C TWIPMAAXAROIGN-UHFFFAOYSA-N 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 6
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 2
YXBURMMYJOWGPB-UHFFFAOYSA-N 3-cyclohexylpropyl 1-(3,3-dimethyl-2-oxobutanoyl)piperidine-2-carboxylate Chemical compound CC(C)(C)C(=O)C(=O)N1CCCCC1C(=O)OCCCC1CCCCC1 YXBURMMYJOWGPB-UHFFFAOYSA-N 0.000 claims 2
OQVHIQBTTGZGJM-UHFFFAOYSA-N 3-phenylpropyl 1-(2-cyclohexyl-2-oxoacetyl)piperidine-2-carboxylate Chemical compound C1CCCN(C(=O)C(=O)C2CCCCC2)C1C(=O)OCCCC1=CC=CC=C1 OQVHIQBTTGZGJM-UHFFFAOYSA-N 0.000 claims 2
JZURKRWBHAEVQM-UHFFFAOYSA-N 3-phenylpropyl 1-(2-oxo-2-phenylacetyl)piperidine-2-carboxylate Chemical compound C1CCCN(C(=O)C(=O)C=2C=CC=CC=2)C1C(=O)OCCCC1=CC=CC=C1 JZURKRWBHAEVQM-UHFFFAOYSA-N 0.000 claims 2
BZXRDDWHRLMZAZ-UHFFFAOYSA-N 3-phenylpropyl 1-(3,3-dimethyl-2-oxobutanoyl)piperidine-2-carboxylate Chemical compound CC(C)(C)C(=O)C(=O)N1CCCCC1C(=O)OCCCC1=CC=CC=C1 BZXRDDWHRLMZAZ-UHFFFAOYSA-N 0.000 claims 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 2
DZIVTOOJQNAGGM-UHFFFAOYSA-N ethyl 1-(2-cyclohexyl-2-oxoacetyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)C1CCCCC1 DZIVTOOJQNAGGM-UHFFFAOYSA-N 0.000 claims 2
LMKBKBZKCHJCQA-UHFFFAOYSA-N ethyl 1-(2-oxobutanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)CC LMKBKBZKCHJCQA-UHFFFAOYSA-N 0.000 claims 2
HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims 2
DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 2
HPAXNUBJQISTTA-UHFFFAOYSA-N 1-(2-cyclohexyl-2-oxoacetyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CCCCN1C(=O)C(=O)C1CCCCC1 HPAXNUBJQISTTA-UHFFFAOYSA-N 0.000 claims 1
JMAXMSHFUIHSAO-UHFFFAOYSA-N 3,4-diphenylpentyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCCC1C(=O)OCCC(C=1C=CC=CC=1)C(C)C1=CC=CC=C1 JMAXMSHFUIHSAO-UHFFFAOYSA-N 0.000 claims 1
UKRQXJTZXSEWIU-UHFFFAOYSA-N 3-cyclohexylpropyl 1-(2-cyclohexyl-2-oxoacetyl)piperidine-2-carboxylate Chemical compound C1CCCN(C(=O)C(=O)C2CCCCC2)C1C(=O)OCCCC1CCCCC1 UKRQXJTZXSEWIU-UHFFFAOYSA-N 0.000 claims 1
KAKARIMHVBDECO-UHFFFAOYSA-N 3-ethylpiperidine-1-carboxylic acid Chemical compound CCC1CCCN(C1)C(O)=O KAKARIMHVBDECO-UHFFFAOYSA-N 0.000 claims 1
LZMJPLNFPWMYJE-SFHVURJKSA-N 3-phenylpropyl (2s)-1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCC[C@H]1C(=O)OCCCC1=CC=CC=C1 LZMJPLNFPWMYJE-SFHVURJKSA-N 0.000 claims 1
OTRNZHCNNPSPJM-UHFFFAOYSA-N 3-phenylpropyl 1-(2-hydroxy-3,3-dimethylpentanoyl)piperidine-2-carboxylate Chemical compound CCC(C)(C)C(O)C(=O)N1CCCCC1C(=O)OCCCC1=CC=CC=C1 OTRNZHCNNPSPJM-UHFFFAOYSA-N 0.000 claims 1
FUFFLVUDCWMXJX-UHFFFAOYSA-N 4-(4-methoxyphenyl)butyl 1-(2-oxo-2-phenylacetyl)piperidine-2-carboxylate Chemical compound C1=CC(OC)=CC=C1CCCCOC(=O)C1N(C(=O)C(=O)C=2C=CC=CC=2)CCCC1 FUFFLVUDCWMXJX-UHFFFAOYSA-N 0.000 claims 1
GTZVYGLYWWKLLR-UHFFFAOYSA-N CCCOC(=O)C1CCCCN1C(=O)C(=O)C(C)(C)CC Chemical compound CCCOC(=O)C1CCCCN1C(=O)C(=O)C(C)(C)CC GTZVYGLYWWKLLR-UHFFFAOYSA-N 0.000 claims 1
XEGSHDSXEIFRLI-UHFFFAOYSA-N [1-(4-methoxyphenyl)-6-phenylhexan-3-yl] 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate Chemical compound CCC(C)(C)C(=O)C(=O)N1CCCCC1C(=O)OC(CCC=1C=CC(OC)=CC=1)CCCC1=CC=CC=C1 XEGSHDSXEIFRLI-UHFFFAOYSA-N 0.000 claims 1
150000007942 carboxylates Chemical class 0.000 claims 1
KDJAKBJRDJBEOI-UHFFFAOYSA-N ethyl 1-(2-oxo-3-phenylpropanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)CC1=CC=CC=C1 KDJAKBJRDJBEOI-UHFFFAOYSA-N 0.000 claims 1
UGLHVWLPNYTJDX-UHFFFAOYSA-N ethyl 1-(2-oxopropanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(C)=O UGLHVWLPNYTJDX-UHFFFAOYSA-N 0.000 claims 1
CAXFSIWSCHLEMR-UHFFFAOYSA-N ethyl 1-(3,3-dimethyl-2-oxopentanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)C(C)(C)CC CAXFSIWSCHLEMR-UHFFFAOYSA-N 0.000 claims 1
AWDVACRNZJJBAN-UHFFFAOYSA-N ethyl 1-(4-acetyloxy-3,3-dimethyl-2-oxobutanoyl)piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)C(C)(C)COC(C)=O AWDVACRNZJJBAN-UHFFFAOYSA-N 0.000 claims 1
BIZAQJIRMUXGHM-UHFFFAOYSA-N ethyl 1-[2-(1-hydroxycyclohexyl)-2-oxoacetyl]piperidine-2-carboxylate Chemical compound CCOC(=O)C1CCCCN1C(=O)C(=O)C1(O)CCCCC1 BIZAQJIRMUXGHM-UHFFFAOYSA-N 0.000 claims 1
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