SK16662000A3 - Alifatické aminokarboxylové a aminofosfónové kyseliny, aminonitrily a aminotetrazoly ako bunkové záchranné činidlá - Google Patents

Alifatické aminokarboxylové a aminofosfónové kyseliny, aminonitrily a aminotetrazoly ako bunkové záchranné činidlá Download PDF

Info

Publication number: SK16662000A3
Authority: SK; Slovakia
Prior art keywords: acid; heptylamino; acetonitrile; heptylmethylamino; methyl
Prior art date: 1998-03-26

Application number

SK1666-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Zosnul� Paterson I. Alick

Lilian E. Dyck

Bruce A. Davis

Ya-Dong Liu

David A. Durden

Alan A. Boulton

Original Assignee

University Of Saskatchewan Technologies Inc.

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.)

1998-03-26

Filing date

1999-03-25

Publication date

2001-05-10

1999-03-25 Application filed by University Of Saskatchewan Technologies Inc. filed Critical University Of Saskatchewan Technologies Inc.

2001-05-10 Publication of SK16662000A3 publication Critical patent/SK16662000A3/sk

Links

239000003795 chemical substances by application Substances 0.000 title abstract description 10
230000001413 cellular effect Effects 0.000 title abstract description 3
125000005219 aminonitrile group Chemical group 0.000 title description 7
ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical class NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 title description 5
PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical class NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 67
-1 phosphonate ester Chemical class 0.000 claims abstract description 62
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 34
150000003839 salts Chemical class 0.000 claims abstract description 26
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 21
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims abstract description 20
YMRIDJQAEZFTSC-UHFFFAOYSA-N 2,3-dihydro-1h-tetrazole Chemical compound N1NC=NN1 YMRIDJQAEZFTSC-UHFFFAOYSA-N 0.000 claims abstract description 13
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 38
230000006907 apoptotic process Effects 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 15
230000030833 cell death Effects 0.000 claims description 12
FKHDHAIECZZSDD-SNVBAGLBSA-N 3-[[(2r)-heptan-2-yl]amino]propanenitrile Chemical compound CCCCC[C@@H](C)NCCC#N FKHDHAIECZZSDD-SNVBAGLBSA-N 0.000 claims description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
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125000004423 acyloxy group Chemical group 0.000 claims description 5
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
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125000001424 substituent group Chemical group 0.000 claims description 5
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150000003457 sulfones Chemical class 0.000 claims description 5
150000003462 sulfoxides Chemical class 0.000 claims description 5
ZHABVKVHMOPJPW-UHFFFAOYSA-N 2-(heptylamino)acetic acid Chemical compound CCCCCCCNCC(O)=O ZHABVKVHMOPJPW-UHFFFAOYSA-N 0.000 claims description 4
MAOJCYZYVVIJEE-UHFFFAOYSA-N 2-(heptylamino)acetonitrile Chemical compound CCCCCCCNCC#N MAOJCYZYVVIJEE-UHFFFAOYSA-N 0.000 claims description 4
GEHLSZHBGRYZLO-UHFFFAOYSA-N 2-(propan-2-ylamino)ethylphosphonic acid Chemical compound CC(C)NCCP(O)(O)=O GEHLSZHBGRYZLO-UHFFFAOYSA-N 0.000 claims description 4
VOERWDRIENHWPM-SSDOTTSWSA-N 2-[[(2r)-pentan-2-yl]amino]acetonitrile Chemical compound CCC[C@@H](C)NCC#N VOERWDRIENHWPM-SSDOTTSWSA-N 0.000 claims description 4
AHYKKFYHEKHFLH-SSDOTTSWSA-N 2-[[(2r)-pentan-2-yl]amino]ethylphosphonic acid Chemical compound CCC[C@@H](C)NCCP(O)(O)=O AHYKKFYHEKHFLH-SSDOTTSWSA-N 0.000 claims description 4
GHXOCXICYPEHHL-VIFPVBQESA-N 2-[[(2s)-heptan-2-yl]-methylamino]acetic acid Chemical compound CCCCC[C@H](C)N(C)CC(O)=O GHXOCXICYPEHHL-VIFPVBQESA-N 0.000 claims description 4
XAZICOBYASVISU-QMMMGPOBSA-N 2-[[(2s)-heptan-2-yl]amino]acetic acid Chemical compound CCCCC[C@H](C)NCC(O)=O XAZICOBYASVISU-QMMMGPOBSA-N 0.000 claims description 4
LNSHSMZFSMMYGL-VIFPVBQESA-N 2-[[(2s)-heptan-2-yl]amino]ethylphosphonic acid Chemical compound CCCCC[C@H](C)NCCP(O)(O)=O LNSHSMZFSMMYGL-VIFPVBQESA-N 0.000 claims description 4
ARUDWQMVVFUBLR-UHFFFAOYSA-N 2-[methyl(propan-2-yl)amino]ethylphosphonic acid Chemical compound CC(C)N(C)CCP(O)(O)=O ARUDWQMVVFUBLR-UHFFFAOYSA-N 0.000 claims description 4
YNKQGDGOWRTKNM-MRVPVSSYSA-N 2-[methyl-[(2r)-pentan-2-yl]amino]acetonitrile Chemical compound CCC[C@@H](C)N(C)CC#N YNKQGDGOWRTKNM-MRVPVSSYSA-N 0.000 claims description 4
ZIRMOWIHYLRAAM-SNVBAGLBSA-N 3-[[(2r)-heptan-2-yl]-methylamino]propanoic acid Chemical compound CCCCC[C@@H](C)N(C)CCC(O)=O ZIRMOWIHYLRAAM-SNVBAGLBSA-N 0.000 claims description 4
XALDKEZPZCTUSC-SECBINFHSA-N 3-[[(2r)-heptan-2-yl]amino]propanoic acid Chemical compound CCCCC[C@@H](C)NCCC(O)=O XALDKEZPZCTUSC-SECBINFHSA-N 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
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HLDVEZAGFUBIFC-UHFFFAOYSA-N 2-(hexylamino)acetonitrile Chemical compound CCCCCCNCC#N HLDVEZAGFUBIFC-UHFFFAOYSA-N 0.000 claims description 3
FOWHYYRXKJOHJB-JTQLQIEISA-N 2-[[(2s)-heptan-2-yl]-methylamino]acetonitrile Chemical compound CCCCC[C@H](C)N(C)CC#N FOWHYYRXKJOHJB-JTQLQIEISA-N 0.000 claims description 3
OPOKOMZAOJEEBD-VIFPVBQESA-N 2-[[(2s)-heptan-2-yl]amino]acetonitrile Chemical compound CCCCC[C@H](C)NCC#N OPOKOMZAOJEEBD-VIFPVBQESA-N 0.000 claims description 3
ZOGOTIIKBRFGIO-UHFFFAOYSA-N 3-[methyl(propan-2-yl)azaniumyl]propanoate Chemical compound CC(C)N(C)CCC(O)=O ZOGOTIIKBRFGIO-UHFFFAOYSA-N 0.000 claims description 3
208000002249 Diabetes Complications Diseases 0.000 claims description 3
206010012655 Diabetic complications Diseases 0.000 claims description 3
241000270322 Lepidosauria Species 0.000 claims description 3
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206010038923 Retinopathy Diseases 0.000 claims description 3
230000000747 cardiac effect Effects 0.000 claims description 3
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230000007823 neuropathy Effects 0.000 claims description 3
201000001119 neuropathy Diseases 0.000 claims description 3
208000033808 peripheral neuropathy Diseases 0.000 claims description 3
DAQPDSNNUNDKNX-UHFFFAOYSA-N 2-(hexylamino)acetic acid Chemical compound CCCCCCNCC(O)=O DAQPDSNNUNDKNX-UHFFFAOYSA-N 0.000 claims description 2
KCMLHEAFFIUPAW-UHFFFAOYSA-N 2-(propan-2-ylamino)acetonitrile Chemical compound CC(C)NCC#N KCMLHEAFFIUPAW-UHFFFAOYSA-N 0.000 claims description 2
HEPOIJKOXBKKNJ-UHFFFAOYSA-N 2-(propan-2-ylazaniumyl)acetate Chemical compound CC(C)NCC(O)=O HEPOIJKOXBKKNJ-UHFFFAOYSA-N 0.000 claims description 2
RMLIHPQMHVOHNZ-UHFFFAOYSA-N 2-[methyl(propan-2-yl)azaniumyl]acetate Chemical compound CC(C)N(C)CC(O)=O RMLIHPQMHVOHNZ-UHFFFAOYSA-N 0.000 claims description 2
YLLULQCFYBZRIZ-UHFFFAOYSA-N 3-(heptylamino)propanoic acid Chemical compound CCCCCCCNCCC(O)=O YLLULQCFYBZRIZ-UHFFFAOYSA-N 0.000 claims description 2
GJVVIWWPEAZPHI-UHFFFAOYSA-N 3-(hexylamino)propanoic acid Chemical compound CCCCCCNCCC(O)=O GJVVIWWPEAZPHI-UHFFFAOYSA-N 0.000 claims description 2
AKSSCYRRVNHNDF-UHFFFAOYSA-N 3-(propan-2-ylamino)propanoic acid Chemical compound CC(C)NCCC(O)=O AKSSCYRRVNHNDF-UHFFFAOYSA-N 0.000 claims description 2
206010012667 Diabetic glaucoma Diseases 0.000 claims description 2
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FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 2
UVUNWXZEMDFNEI-JTQLQIEISA-N 2-[[(2s)-heptan-2-yl]-methylamino]ethylphosphonic acid Chemical compound CCCCC[C@H](C)N(C)CCP(O)(O)=O UVUNWXZEMDFNEI-JTQLQIEISA-N 0.000 claims 3
VQLGYYPEOITXBW-LLVKDONJSA-N 3-[[(2r)-heptan-2-yl]-methylamino]propanenitrile Chemical compound CCCCC[C@@H](C)N(C)CCC#N VQLGYYPEOITXBW-LLVKDONJSA-N 0.000 claims 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
YZOXTDXTQNCIAY-MRVPVSSYSA-N 2-[methyl-[(2r)-pentan-2-yl]amino]ethylphosphonic acid Chemical compound CCC[C@@H](C)N(C)CCP(O)(O)=O YZOXTDXTQNCIAY-MRVPVSSYSA-N 0.000 claims 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
OKVCJTAEKCLWKS-UHFFFAOYSA-N 2-[methyl(propan-2-yl)amino]acetonitrile Chemical compound CC(C)N(C)CC#N OKVCJTAEKCLWKS-UHFFFAOYSA-N 0.000 claims 1
MWQQQTMDMMVPQA-UHFFFAOYSA-N 3-(pentan-3-ylamino)propanenitrile Chemical compound CCC(CC)NCCC#N MWQQQTMDMMVPQA-UHFFFAOYSA-N 0.000 claims 1
AKWOWRDFRFDMHC-UHFFFAOYSA-N 3-[methyl(pentan-3-yl)amino]propanenitrile Chemical compound CCC(CC)N(C)CCC#N AKWOWRDFRFDMHC-UHFFFAOYSA-N 0.000 claims 1
208000020446 Cardiac disease Diseases 0.000 claims 1
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IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 claims 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract description 7
125000001931 aliphatic group Chemical group 0.000 abstract description 3
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238000001819 mass spectrum Methods 0.000 description 38
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239000007864 aqueous solution Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
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238000010931 ester hydrolysis Methods 0.000 description 1
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239000001963 growth medium Substances 0.000 description 1
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238000001727 in vivo Methods 0.000 description 1
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FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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239000002207 metabolite Substances 0.000 description 1
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150000004702 methyl esters Chemical class 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
239000007923 nasal drop Substances 0.000 description 1
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230000004770 neurodegeneration Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
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JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
150000003139 primary aliphatic amines Chemical class 0.000 description 1
WGWKNMLSVLOQJB-UHFFFAOYSA-N propan-2-ylazanium;bromide Chemical compound Br.CC(C)N WGWKNMLSVLOQJB-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 1
229960000245 rasagiline Drugs 0.000 description 1
238000006485 reductive methylation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical compound C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 1
KIMPPGSMONZDMN-UHFFFAOYSA-N sodium;dihydrogen phosphite Chemical compound [Na+].OP(O)[O-] KIMPPGSMONZDMN-UHFFFAOYSA-N 0.000 description 1
208000020431 spinal cord injury Diseases 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
XJPANWOKBWZVHC-UHFFFAOYSA-N tetrazol-2-amine Chemical compound NN1N=CN=N1 XJPANWOKBWZVHC-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000005583 trifluoroacetylation reaction Methods 0.000 description 1
NCPXQVVMIXIKTN-UHFFFAOYSA-N trisodium;phosphite Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])[O-] NCPXQVVMIXIKTN-UHFFFAOYSA-N 0.000 description 1
ZTWTYVWXUKTLCP-UHFFFAOYSA-N vinylphosphonic acid Chemical class OP(O)(=O)C=C ZTWTYVWXUKTLCP-UHFFFAOYSA-N 0.000 description 1
150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1

Classifications

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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/24—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same saturated acyclic carbon skeleton
- C07C255/25—Aminoacetonitriles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

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SK1666-2000A 1998-03-26 1999-03-25 Alifatické aminokarboxylové a aminofosfónové kyseliny, aminonitrily a aminotetrazoly ako bunkové záchranné činidlá SK16662000A3 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US7948898P	1998-03-26	1998-03-26
US7948998P	1998-03-26	1998-03-26
PCT/CA1999/000250 WO1999048858A2 (en)	1998-03-26	1999-03-25	Aliphatic amino carboxylic and amino phosphonic acids, amino nitriles and amino tetrazoles as cellular rescue agents

Publications (1)

Publication Number	Publication Date
SK16662000A3 true SK16662000A3 (sk)	2001-05-10

Family

ID=26762066

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1666-2000A SK16662000A3 (sk)	1998-03-26	1999-03-25	Alifatické aminokarboxylové a aminofosfónové kyseliny, aminonitrily a aminotetrazoly ako bunkové záchranné činidlá

Country Status (15)

Country	Link
EP (1)	EP1064254B1 (de)
JP (1)	JP2002507591A (de)
CN (1)	CN1213999C (de)
AT (1)	ATE375975T1 (de)
AU (1)	AU767098B2 (de)
BR (1)	BR9909103A (de)
CA (1)	CA2325943A1 (de)
DE (1)	DE69937340T2 (de)
EA (1)	EA003677B1 (de)
ES (1)	ES2296383T3 (de)
NO (1)	NO20004774D0 (de)
PL (1)	PL343531A1 (de)
SK (1)	SK16662000A3 (de)
TR (1)	TR200002756T2 (de)
WO (1)	WO1999048858A2 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20230065740A1 (en)	2018-12-28	2023-03-02	Spv Therapeutics Inc.	Cyclin-dependent kinase inhibitors

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3113026A (en) *	1959-01-19	1963-12-03	Gen Aniline & Film Corp	Polyvinyl alcohol photographic silver halide emulsions
DE1567221A1 (de) *	1965-06-01	1970-04-16	Berlin Chemie Veb	Systemische Fungizide
BE758165A (fr) *	1969-10-28	1971-04-28	Cilag Chemie	Adamantylurees et procedes pour les preparer
IL45563A0 (en) *	1973-09-05	1974-11-29	Sumitomo Chemical Co	N-substituted aminonitrile derivatives,their preparation and their use as fungicides
US3991208A (en) *	1973-12-28	1976-11-09	Millmaster Onyx Corporation	Amphoteric surface-active agents
DE2555769C3 (de) *	1975-12-11	1980-01-03	Basf Ag, 6700 Ludwigshafen	Verfahren zur Herstellung von an der Aminogruppe aliphatisch substituierten Glycinnitrilen
DE3010599A1 (de) *	1979-03-22	1980-10-09	Continental Pharma	Derivate von glycinamid, deren herstellung und verwendung
US4548726A (en) *	1984-11-16	1985-10-22	Texaco Inc.	Water base hydraulic fluid
KR930005009B1 (ko) *	1990-03-27	1993-06-11	한국과학기술연구원	N-알킬치환아미노메틸포스폰산 유도체의 제조방법
US5169868A (en) *	1991-03-01	1992-12-08	University Of Saskatchewan	Aliphatic propargylamines as specific mao-b inhibitors
JPH0856655A (ja) *	1994-08-16	1996-03-05	Frontier:Kk	細胞致死剤および細胞死抑制剤
CZ294348B6 (cs) *	1996-05-31	2004-12-15	Allelix Neuroscience Inc.	Substituovaný derivát glycinu a farmaceutický prostředek s jeho obsahem

1999
- 1999-03-25 ES ES99908728T patent/ES2296383T3/es not_active Expired - Lifetime
- 1999-03-25 EA EA200000987A patent/EA003677B1/ru not_active IP Right Cessation
- 1999-03-25 DE DE69937340T patent/DE69937340T2/de not_active Expired - Fee Related
- 1999-03-25 CN CNB998056383A patent/CN1213999C/zh not_active Expired - Fee Related
- 1999-03-25 EP EP99908728A patent/EP1064254B1/de not_active Expired - Lifetime
- 1999-03-25 TR TR2000/02756T patent/TR200002756T2/xx unknown
- 1999-03-25 AT AT99908728T patent/ATE375975T1/de not_active IP Right Cessation
- 1999-03-25 AU AU28240/99A patent/AU767098B2/en not_active Ceased
- 1999-03-25 BR BR9909103-8A patent/BR9909103A/pt not_active IP Right Cessation
- 1999-03-25 SK SK1666-2000A patent/SK16662000A3/sk unknown
- 1999-03-25 WO PCT/CA1999/000250 patent/WO1999048858A2/en not_active Ceased
- 1999-03-25 JP JP2000537843A patent/JP2002507591A/ja active Pending
- 1999-03-25 PL PL99343531A patent/PL343531A1/xx not_active Application Discontinuation
- 1999-03-25 CA CA002325943A patent/CA2325943A1/en not_active Abandoned
2000
- 2000-09-25 NO NO20004774A patent/NO20004774D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE69937340D1 (de)	2007-11-29
NO20004774L (no)	2000-09-25
PL343531A1 (en)	2001-08-27
CN1299342A (zh)	2001-06-13
EP1064254B1 (de)	2007-10-17
NO20004774D0 (no)	2000-09-25
DE69937340T2 (de)	2008-07-17
JP2002507591A (ja)	2002-03-12
WO1999048858A2 (en)	1999-09-30
ES2296383T3 (es)	2008-04-16
EA003677B1 (ru)	2003-08-28
EP1064254A2 (de)	2001-01-03
AU2824099A (en)	1999-10-18
EA200000987A1 (ru)	2001-06-25
ATE375975T1 (de)	2007-11-15
CN1213999C (zh)	2005-08-10
TR200002756T2 (tr)	2000-12-21
WO1999048858A3 (en)	2000-01-20
CA2325943A1 (en)	1999-09-30
AU767098B2 (en)	2003-10-30
BR9909103A (pt)	2001-10-16

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US20170119702A1 (en)	2017-05-04	Dosage Regimen of Diaryl Sulfide Derivatives
MXPA00009495A (en)	2002-03-05	Aliphatic amino carboxylic and amino phosphonic acids, amino nitriles and amino tetrazoles as cellular rescue agents
EP0172059B1 (de)	1988-04-20	Oxaazaphosphorin-Derivate, Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zubereitungen
WO2003011856A1 (fr)	2003-02-13	Derives d'aminoalkylimidazole, leur preparation et leur utilisation en therapeutique