SK282069B6 - Deriváty aminokyselín so zlepšenou rezistenciou proti viacerým liečivám, farmaceutická kompozícia, ktorá ich obsahuje, ich použitie a spôsob ich prípravy - Google Patents

Deriváty aminokyselín so zlepšenou rezistenciou proti viacerým liečivám, farmaceutická kompozícia, ktorá ich obsahuje, ich použitie a spôsob ich prípravy Download PDF

Info

Publication number: SK282069B6
Authority: SK; Slovakia
Prior art keywords: carbon atoms; group; straight; branched chain; pyr
Prior art date: 1994-11-16

Application number

SK611-97A

Other languages

English (en)

Slovak (sk)

Other versions

SK61197A3 (en

Inventor

Robert E. Zelle

Matthew W. Harding

Original Assignee

Vertex Pharmaceuticals Incorporated

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

1994-11-16

Filing date

1995-11-13

Publication date

2001-10-08

1995-01-23 Priority claimed from US08/377,285 external-priority patent/US5543423A/en

1995-11-13 Application filed by Vertex Pharmaceuticals Incorporated filed Critical Vertex Pharmaceuticals Incorporated

1997-11-05 Publication of SK61197A3 publication Critical patent/SK61197A3/sk

2001-10-08 Publication of SK282069B6 publication Critical patent/SK282069B6/sk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 20
238000000034 method Methods 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 6
150000003862 amino acid derivatives Chemical class 0.000 title claims 9
150000001875 compounds Chemical class 0.000 claims abstract description 98
239000003814 drug Substances 0.000 claims abstract description 26
230000036457 multidrug resistance Effects 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 81
-1 3-firryl Chemical group 0.000 claims description 65
125000000217 alkyl group Chemical group 0.000 claims description 56
125000003342 alkenyl group Chemical group 0.000 claims description 31
125000000304 alkynyl group Chemical group 0.000 claims description 20
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 13
229910052757 nitrogen Inorganic materials 0.000 claims description 13
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
229940080818 propionamide Drugs 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
102100033350 ATP-dependent translocase ABCB1 Human genes 0.000 claims description 9
108010047230 Member 1 Subfamily B ATP Binding Cassette Transporter Proteins 0.000 claims description 9
125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
150000001413 amino acids Chemical class 0.000 claims description 6
239000002246 antineoplastic agent Substances 0.000 claims description 6
125000002883 imidazolyl group Chemical group 0.000 claims description 6
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230000003034 chemosensitisation Effects 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
230000008878 coupling Effects 0.000 claims description 4
238000010168 coupling process Methods 0.000 claims description 4
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125000000753 cycloalkyl group Chemical group 0.000 claims description 4
229940127089 cytotoxic agent Drugs 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
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239000011593 sulfur Chemical group 0.000 claims description 4
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229910052799 carbon Inorganic materials 0.000 claims description 3
125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims description 3
239000006114 chemosensitizer Substances 0.000 claims description 3
125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
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GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 3
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239000003981 vehicle Substances 0.000 claims description 3
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
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125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
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125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical group C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 2
125000003828 azulenyl group Chemical group 0.000 claims description 2
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125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
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125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
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125000000168 pyrrolyl group Chemical group 0.000 claims description 2
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DNNVRTZJRKIUFK-UHFFFAOYSA-N 3,4-dihydroquinoline Chemical class C1=CC=C2N=CCCC2=C1 DNNVRTZJRKIUFK-UHFFFAOYSA-N 0.000 claims 1
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
125000005936 piperidyl group Chemical group 0.000 claims 1
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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 1
229960002930 sirolimus Drugs 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000003440 toxic substance Substances 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
241001430294 unidentified retrovirus Species 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
229960003048 vinblastine Drugs 0.000 description 1
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
239000003643 water by type Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Thiazole And Isothizaole Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Peptides Or Proteins (AREA)

SK611-97A 1994-11-16 1995-11-13 Deriváty aminokyselín so zlepšenou rezistenciou proti viacerým liečivám, farmaceutická kompozícia, ktorá ich obsahuje, ich použitie a spôsob ich prípravy SK282069B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US34083094A	1994-11-16	1994-11-16
US08/377,285 US5543423A (en)	1994-11-16	1995-01-23	Amino acid derivatives with improved multi-drug resistance activity
PCT/US1995/014841 WO1996015101A1 (fr)	1994-11-16	1995-11-13	Nouveaux derives d'acides amines presentant une meilleure activite contre la resistance a plusieurs medicaments

Publications (2)

Publication Number	Publication Date
SK61197A3 SK61197A3 (en)	1997-11-05
SK282069B6 true SK282069B6 (sk)	2001-10-08

Family

ID=26992255

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK611-97A SK282069B6 (sk)	1994-11-16	1995-11-13	Deriváty aminokyselín so zlepšenou rezistenciou proti viacerým liečivám, farmaceutická kompozícia, ktorá ich obsahuje, ich použitie a spôsob ich prípravy

Country Status (24)

Country	Link
EP (1)	EP0797567B1 (fr)
JP (1)	JP3921239B2 (fr)
AP (1)	AP781A (fr)
AT (1)	ATE259349T1 (fr)
AU (1)	AU689991B2 (fr)
BR (1)	BR9509698A (fr)
CA (1)	CA2224198A1 (fr)
CZ (1)	CZ298586B6 (fr)
DE (1)	DE69532561T2 (fr)
DK (1)	DK0797567T3 (fr)
ES (1)	ES2216022T3 (fr)
FI (1)	FI972086A7 (fr)
HU (1)	HU226136B1 (fr)
IL (1)	IL115685A (fr)
MX (1)	MX9703621A (fr)
NO (1)	NO323292B1 (fr)
NZ (2)	NZ296474A (fr)
PL (1)	PL182327B1 (fr)
PT (1)	PT797567E (fr)
RO (1)	RO121113B1 (fr)
SI (1)	SI0797567T1 (fr)
SK (1)	SK282069B6 (fr)
TJ (1)	TJ321B (fr)
WO (1)	WO1996015101A1 (fr)

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US5846981A (en) *	1993-05-28	1998-12-08	Gpi Nil Holdings Inc.	Inhibitors of rotamase enzyme activity
US5798355A (en) *	1995-06-07	1998-08-25	Gpi Nil Holdings, Inc.	Inhibitors of rotamase enzyme activity
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
US5801197A (en) *	1995-10-31	1998-09-01	Gpi Nil Holdings, Inc.	Rotamase enzyme activity inhibitors
US5786378A (en) *	1996-09-25	1998-07-28	Gpi Nil Holdings, Inc.	Heterocyclic thioesters
US6218424B1 (en)	1996-09-25	2001-04-17	Gpi Nil Holdings, Inc.	Heterocyclic ketone and thioester compounds and uses
US5801187A (en)	1996-09-25	1998-09-01	Gpi-Nil Holdings, Inc.	Heterocyclic esters and amides
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
US6242468B1 (en) *	1997-02-27	2001-06-05	Jia-He Li	Carbamate and urea compositions and neurotrophic uses
US5846979A (en) *	1997-02-28	1998-12-08	Gpi Nil Holdings, Inc.	N-oxides of heterocyclic esters, amides, thioesters, and ketones
US20010049381A1 (en)	1997-06-04	2001-12-06	Gpl Nil Holdings, Inc.,	Pyrrolidine derivative hair growth compositions and uses
US6268384B1 (en)	1997-08-29	2001-07-31	Vertex Pharmaceuticals Incorporated	Compounds possessing neuronal activity
US6331537B1 (en)	1998-06-03	2001-12-18	Gpi Nil Holdings, Inc.	Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds
EP1083875A1 (fr) *	1998-06-03	2001-03-21	GPI NIL Holdings, Inc.	Compositions pour la croissance des cheveux a base de petites molecules de carbamates ou d'urees et utilisation de ces compositions
US6376517B1 (en)	1998-08-14	2002-04-23	Gpi Nil Holdings, Inc.	Pipecolic acid derivatives for vision and memory disorders
US6384056B1 (en)	1998-08-14	2002-05-07	Gpi Nil Holdings, Inc.	Heterocyclic thioesters or ketones for vision and memory disorders
US6506788B1 (en)	1998-08-14	2003-01-14	Gpi Nil Holdings, Inc.	N-linked urea or carbamate of heterocyclic thioesters for vision and memory disorders
US6218423B1 (en)	1998-08-14	2001-04-17	Gpi Nil Holdings, Inc.	Pyrrolidine derivatives for vision and memory disorders
US6333340B1 (en)	1998-08-14	2001-12-25	Gpi Nil Holdings, Inc.	Small molecule sulfonamides for vision and memory disorders
US6335348B1 (en)	1998-08-14	2002-01-01	Gpi Nil Holdings, Inc.	Nitrogen-containing linear and azepinyl/ compositions and uses for vision and memory disorders
US6337340B1 (en)	1998-08-14	2002-01-08	Gpi Nil Holdings, Inc.	Carboxylic acids and isosteres of heterocyclic ring compounds having multiple heteroatoms for vision and memory disorders
US7338976B1 (en)	1998-08-14	2008-03-04	Gpi Nil Holdings, Inc.	Heterocyclic esters or amides for vision and memory disorders
US6339101B1 (en)	1998-08-14	2002-01-15	Gpi Nil Holdings, Inc.	N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders
US6399648B1 (en)	1998-08-14	2002-06-04	Gpi Nil Holdings, Inc.	N-oxides of heterocyclic ester, amide, thioester, or ketone for vision and memory disorders
US6395758B1 (en)	1998-08-14	2002-05-28	Gpi Nil Holdings, Inc.	Small molecule carbamates or ureas for vision and memory disorders
US6462072B1 (en)	1998-09-21	2002-10-08	Gpi Nil Holdings, Inc.	Cyclic ester or amide derivatives
US6300341B1 (en)	1998-09-30	2001-10-09	The Procter & Gamble Co.	2-substituted heterocyclic sulfonamides
US6307049B1 (en)	1998-09-30	2001-10-23	The Procter & Gamble Co.	Heterocyclic 2-substituted ketoamides
AU6060099A (en) *	1998-09-30	2000-04-17	Procter & Gamble Company, The	2-substituted ketoamides
WO2000040557A1 (fr) *	1999-01-08	2000-07-13	Vertex Pharmaceuticals Incorporated	Procede de formation d'intermediaires utiles a la preparation de produits pharmaceutiques
JP2001031635A (ja) *	1999-07-14	2001-02-06	Ajinomoto Co Inc	光学活性ｎ−保護−ｎ−メチル−フェニルアラニン誘導体の製造方法
US6376514B1 (en)	2000-10-17	2002-04-23	The Procter & Gamble Co.	Substituted six-membered heterocyclic compounds useful for treating multidrug resistance and compositions and methods thereof
US6693099B2 (en)	2000-10-17	2004-02-17	The Procter & Gamble Company	Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance
US7345068B2 (en) *	2002-02-07	2008-03-18	Hitoshi Endou	Aromatic amino acid derivatives and medicinal compositions
MX2012002910A (es)	2009-09-11	2012-04-19	Vertex Pharma	Composiciones de n-bencil-3-(4-clorofenil)-2-[metil-[2-oxo-2-(3,4, 5-trietoxifenil)acetil]amino]-n-[3-(4-piridil)-1-[2-(4-piridil)et il]propil]propanamida y usos de las misma.

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CA2074061A1 (fr) *	1991-08-26	1993-02-27	Ivo Monkovic	Benzamides, agents d'inversion de la resistance multiple aux anti-cancereux
NZ314207A (en) *	1992-09-28	2000-12-22	Vertex Pharma	1-(2-Oxoacetyl)-piperidine-2-carboxylic acid derivatives as multi drug resistant cancer cell sensitizers
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1995
- 1995-10-19 IL IL11568595A patent/IL115685A/xx not_active IP Right Cessation
- 1995-11-13 SK SK611-97A patent/SK282069B6/sk not_active IP Right Cessation
- 1995-11-13 RO RO97-00899A patent/RO121113B1/ro unknown
- 1995-11-13 DK DK95939156T patent/DK0797567T3/da active
- 1995-11-13 ES ES95939156T patent/ES2216022T3/es not_active Expired - Lifetime
- 1995-11-13 BR BR9509698A patent/BR9509698A/pt not_active IP Right Cessation
- 1995-11-13 NZ NZ296474A patent/NZ296474A/xx not_active IP Right Cessation
- 1995-11-13 AP APAP/P/1997/000999A patent/AP781A/en active
- 1995-11-13 TJ TJ97000470A patent/TJ321B/xx unknown
- 1995-11-13 CA CA002224198A patent/CA2224198A1/fr not_active Abandoned
- 1995-11-13 PT PT95939156T patent/PT797567E/pt unknown
- 1995-11-13 CZ CZ0149197A patent/CZ298586B6/cs not_active IP Right Cessation
- 1995-11-13 AU AU41099/96A patent/AU689991B2/en not_active Ceased
- 1995-11-13 MX MX9703621A patent/MX9703621A/es not_active IP Right Cessation
- 1995-11-13 EP EP95939156A patent/EP0797567B1/fr not_active Expired - Lifetime
- 1995-11-13 JP JP51630696A patent/JP3921239B2/ja not_active Expired - Fee Related
- 1995-11-13 DE DE69532561T patent/DE69532561T2/de not_active Expired - Lifetime
- 1995-11-13 PL PL95320227A patent/PL182327B1/pl not_active IP Right Cessation
- 1995-11-13 SI SI9530702T patent/SI0797567T1/xx unknown
- 1995-11-13 FI FI972086A patent/FI972086A7/fi not_active Application Discontinuation
- 1995-11-13 WO PCT/US1995/014841 patent/WO1996015101A1/fr not_active Ceased
- 1995-11-13 HU HU9802168A patent/HU226136B1/hu not_active IP Right Cessation
- 1995-11-13 AT AT95939156T patent/ATE259349T1/de not_active IP Right Cessation
1997
- 1997-05-14 NO NO19972217A patent/NO323292B1/no not_active IP Right Cessation
1998
- 1998-12-15 NZ NZ333373A patent/NZ333373A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
WO1996015101A1 (fr)	1996-05-23
DK0797567T3 (da)	2004-06-14
IL115685A (en)	2000-08-31
ES2216022T3 (es)	2004-10-16
NZ333373A (en)	2000-07-28
TJ321B (en)	2001-10-22
FI972086A0 (fi)	1997-05-15
DE69532561D1 (de)	2004-03-18
PT797567E (pt)	2004-06-30
AP9700999A0 (en)	1997-07-31
PL320227A1 (en)	1997-09-15
AU4109996A (en)	1996-06-06
NO972217D0 (no)	1997-05-14
AP781A (en)	1999-11-04
HUT77977A (hu)	1999-01-28
JP3921239B2 (ja)	2007-05-30
IL115685A0 (en)	1996-01-19
ATE259349T1 (de)	2004-02-15
HK1003636A1 (en)	1998-11-06
HU226136B1 (en)	2008-05-28
RO121113B1 (ro)	2006-12-29
BR9509698A (pt)	1998-06-30
NO323292B1 (no)	2007-03-05
NO972217L (no)	1997-06-17
PL182327B1 (pl)	2001-12-31
SI0797567T1 (en)	2004-06-30
CA2224198A1 (fr)	1996-05-23
AU689991B2 (en)	1998-04-09
CZ298586B6 (cs)	2007-11-14
CZ149197A3 (en)	1997-10-15
MX9703621A (es)	1997-08-30
SK61197A3 (en)	1997-11-05
EP0797567A1 (fr)	1997-10-01
FI972086L (fi)	1997-05-15
EP0797567B1 (fr)	2004-02-11
DE69532561T2 (de)	2004-12-23
JPH10509151A (ja)	1998-09-08
FI972086A7 (fi)	1997-05-15
NZ296474A (en)	1999-01-28

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Publication	Publication Date	Title
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