ZA200505882B - Cyclopropyl beta-amino acid derivatives - Google Patents
Cyclopropyl beta-amino acid derivatives Download PDFInfo
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- ZA200505882B ZA200505882B ZA200505882A ZA200505882A ZA200505882B ZA 200505882 B ZA200505882 B ZA 200505882B ZA 200505882 A ZA200505882 A ZA 200505882A ZA 200505882 A ZA200505882 A ZA 200505882A ZA 200505882 B ZA200505882 B ZA 200505882B
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- South Africa
- Prior art keywords
- pain
- disorders
- disorder
- aminomethyl
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- -1 Cyclopropyl beta-amino acid Chemical class 0.000 title claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 62
- 208000035475 disorder Diseases 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 16
- 208000004296 neuralgia Diseases 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 208000021722 neuropathic pain Diseases 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- YMSSJVJJMKVMQD-UHFFFAOYSA-N 1-(aminomethyl)-2,2-diethylcyclopropane-1-carboxylic acid Chemical compound CCC1(CC)CC1(CN)C(O)=O YMSSJVJJMKVMQD-UHFFFAOYSA-N 0.000 claims description 2
- ZIDXPEFTBREKLG-UHFFFAOYSA-N 1-(aminomethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1(CN)C(O)=O ZIDXPEFTBREKLG-UHFFFAOYSA-N 0.000 claims description 2
- MFQARSDQVCZHFT-UHFFFAOYSA-N 1-(aminomethyl)-2-(2,2-dimethylbutyl)cyclopropane-1-carboxylic acid Chemical compound CCC(C)(C)CC1CC1(CN)C(O)=O MFQARSDQVCZHFT-UHFFFAOYSA-N 0.000 claims description 2
- SLGWMBJANWKJOV-UHFFFAOYSA-N 1-(aminomethyl)-2-(2,2-dimethylhexyl)cyclopropane-1-carboxylic acid Chemical compound CCCCC(C)(C)CC1CC1(CN)C(O)=O SLGWMBJANWKJOV-UHFFFAOYSA-N 0.000 claims description 2
- UDGHYTHRFSZOFK-UHFFFAOYSA-N 1-(aminomethyl)-2-(2,2-dimethylpentyl)cyclopropane-1-carboxylic acid Chemical compound CCCC(C)(C)CC1CC1(CN)C(O)=O UDGHYTHRFSZOFK-UHFFFAOYSA-N 0.000 claims description 2
- VIVULHWBWPFWQD-UHFFFAOYSA-N 1-(aminomethyl)-2-(2-cyclohexylethyl)cyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1CCC1CCCCC1 VIVULHWBWPFWQD-UHFFFAOYSA-N 0.000 claims description 2
- QRDBRFHHNYVCDL-UHFFFAOYSA-N 1-(aminomethyl)-2-(2-methylbutyl)cyclopropane-1-carboxylic acid Chemical compound CCC(C)CC1CC1(CN)C(O)=O QRDBRFHHNYVCDL-UHFFFAOYSA-N 0.000 claims description 2
- PBOPGKAUWXDMIR-UHFFFAOYSA-N 1-(aminomethyl)-2-(2-methylpentyl)cyclopropane-1-carboxylic acid Chemical compound CCCC(C)CC1CC1(CN)C(O)=O PBOPGKAUWXDMIR-UHFFFAOYSA-N 0.000 claims description 2
- PIUMUZORSKNXEJ-UHFFFAOYSA-N 1-(aminomethyl)-2-(2-phenylethyl)cyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1CCC1=CC=CC=C1 PIUMUZORSKNXEJ-UHFFFAOYSA-N 0.000 claims description 2
- IQQFBINOBGINJB-UHFFFAOYSA-N 1-(aminomethyl)-2-(3,7-dimethyloctyl)cyclopropane-1-carboxylic acid Chemical compound CC(C)CCCC(C)CCC1CC1(CN)C(O)=O IQQFBINOBGINJB-UHFFFAOYSA-N 0.000 claims description 2
- IXCQNGWWBUBEKM-UHFFFAOYSA-N 1-(aminomethyl)-2-(3-ethylpentyl)cyclopropane-1-carboxylic acid Chemical compound CCC(CC)CCC1CC1(CN)C(O)=O IXCQNGWWBUBEKM-UHFFFAOYSA-N 0.000 claims description 2
- OZBRHIUYLIMADN-UHFFFAOYSA-N 1-(aminomethyl)-2-(cyclohexylmethyl)cyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1CC1CCCCC1 OZBRHIUYLIMADN-UHFFFAOYSA-N 0.000 claims description 2
- KANVGDSQMSFMIY-UHFFFAOYSA-N 1-(aminomethyl)-2-(cyclopropylmethyl)cyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1CC1CC1 KANVGDSQMSFMIY-UHFFFAOYSA-N 0.000 claims description 2
- GMQVSTQVJLHCMP-UHFFFAOYSA-N 1-(aminomethyl)-2-butylcyclopropane-1-carboxylic acid Chemical compound CCCCC1CC1(CN)C(O)=O GMQVSTQVJLHCMP-UHFFFAOYSA-N 0.000 claims description 2
- JIJHKUYELZUHKJ-UHFFFAOYSA-N 1-(aminomethyl)-2-cyclobutylcyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1C1CCC1 JIJHKUYELZUHKJ-UHFFFAOYSA-N 0.000 claims description 2
- PRPUWXDXEWBAHY-UHFFFAOYSA-N 1-(aminomethyl)-2-cycloheptylcyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1C1CCCCCC1 PRPUWXDXEWBAHY-UHFFFAOYSA-N 0.000 claims description 2
- PMZAJNUCJDXIMT-UHFFFAOYSA-N 1-(aminomethyl)-2-cyclohexylcyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1C1CCCCC1 PMZAJNUCJDXIMT-UHFFFAOYSA-N 0.000 claims description 2
- MCVUJFHLBXTSGE-UHFFFAOYSA-N 1-(aminomethyl)-2-cyclopentylcyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1C1CCCC1 MCVUJFHLBXTSGE-UHFFFAOYSA-N 0.000 claims description 2
- BIRQLZATODDVBN-UHFFFAOYSA-N 1-(aminomethyl)-2-phenylcyclopropane-1-carboxylic acid Chemical compound NCC1(C(O)=O)CC1C1=CC=CC=C1 BIRQLZATODDVBN-UHFFFAOYSA-N 0.000 claims description 2
- LUEYOYPNOZUDTC-UHFFFAOYSA-N 1-(aminomethyl)-2-propan-2-ylcyclopropane-1-carboxylic acid Chemical compound CC(C)C1CC1(CN)C(O)=O LUEYOYPNOZUDTC-UHFFFAOYSA-N 0.000 claims description 2
- AKJJFCPNUBGFKX-UHFFFAOYSA-N 1-(azaniumylmethyl)-2,2-dipropylcyclopropane-1-carboxylate Chemical compound CCCC1(CCC)CC1(CN)C(O)=O AKJJFCPNUBGFKX-UHFFFAOYSA-N 0.000 claims description 2
- RXSIEVRSYDELIV-UHFFFAOYSA-N 1-(azaniumylmethyl)-2-cyclopropylcyclopropane-1-carboxylate Chemical compound NCC1(C(O)=O)CC1C1CC1 RXSIEVRSYDELIV-UHFFFAOYSA-N 0.000 claims description 2
- HRLADBRXOPGTFN-UHFFFAOYSA-N 2-(aminomethyl)-5,6-dimethylspiro[2.4]heptane-2-carboxylic acid Chemical compound C1C(C)C(C)CC11C(C(O)=O)(CN)C1 HRLADBRXOPGTFN-UHFFFAOYSA-N 0.000 claims description 2
- MKDOMRAWQPNCMZ-UHFFFAOYSA-N 2-(aminomethyl)-7-methylspiro[2.5]octane-2-carboxylic acid Chemical compound C1C(C)CCCC11C(C(O)=O)(CN)C1 MKDOMRAWQPNCMZ-UHFFFAOYSA-N 0.000 claims description 2
- OVDIEYUKKNZPEH-UHFFFAOYSA-N 2-(aminomethyl)spiro[2.3]hexane-2-carboxylic acid Chemical compound NCC1(C(O)=O)CC11CCC1 OVDIEYUKKNZPEH-UHFFFAOYSA-N 0.000 claims description 2
- PTMJKTQYTSNXJO-UHFFFAOYSA-N 2-(aminomethyl)spiro[2.6]nonane-2-carboxylic acid Chemical compound NCC1(C(O)=O)CC11CCCCCC1 PTMJKTQYTSNXJO-UHFFFAOYSA-N 0.000 claims description 2
- QLJXULMXXDPJIU-UHFFFAOYSA-N 2-(aminomethyl)spiro[2.7]decane-2-carboxylic acid Chemical compound NCC1(C(O)=O)CC11CCCCCCC1 QLJXULMXXDPJIU-UHFFFAOYSA-N 0.000 claims description 2
- NZSUXZDGKUBVPB-UHFFFAOYSA-N 2-(azaniumylmethyl)spiro[2.5]octane-2-carboxylate Chemical compound NCC1(C(O)=O)CC11CCCCC1 NZSUXZDGKUBVPB-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 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 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
- 125000001475 halogen functional group Chemical group 0.000 claims description 2
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US44182503P | 2003-01-22 | 2003-01-22 |
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ZA200505882B true ZA200505882B (en) | 2006-05-31 |
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ZA200505882A ZA200505882B (en) | 2003-01-22 | 2005-07-21 | Cyclopropyl beta-amino acid derivatives |
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US (1) | US7030267B2 (pl) |
EP (1) | EP1592661A2 (pl) |
JP (1) | JP2006516275A (pl) |
KR (1) | KR100743800B1 (pl) |
CN (1) | CN1764634A (pl) |
AU (1) | AU2004205523A1 (pl) |
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CA (1) | CA2513150A1 (pl) |
IL (1) | IL169488A0 (pl) |
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PL (1) | PL377937A1 (pl) |
RU (1) | RU2312853C2 (pl) |
WO (1) | WO2004065361A2 (pl) |
ZA (1) | ZA200505882B (pl) |
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EA200701782A3 (ru) | 2003-04-24 | 2008-04-28 | Инсайт Корпорейшн | Производные азаспироалканов в качестве ингибиторов металлопротеаз |
RU2468000C2 (ru) * | 2011-03-03 | 2012-11-27 | Запольский Максим Эдуардович | Спироциклические циклопропановые аминокислоты - аналоги гамма-аминомасляной кислоты, с ограниченной конформационной подвижностью и фармацевтические композиции на их основе |
US20140045936A1 (en) | 2011-04-21 | 2014-02-13 | Wake Forest University Health Sciences | Cyclopropyl derivatives and methods of use |
US10287239B1 (en) * | 2018-05-16 | 2019-05-14 | University Of Florida Research Foundation, Inc. | Methods and compositions for terpenoid tricycloalkane synthesis |
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DE2460891C2 (de) * | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
JPH1059801A (ja) * | 1996-06-05 | 1998-03-03 | Otsuka Chem Co Ltd | シクロアルカン誘導体、カルボン酸誘導体及び該誘導体を用いた切り花用鮮度保持剤 |
AU4330097A (en) * | 1996-08-30 | 1998-03-19 | Eli Lilly And Company | Pharmaceutical compounds |
US20020128185A1 (en) * | 1998-02-25 | 2002-09-12 | Chuan Shih | Pharmaceutical compounds |
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2004
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NO20053408L (no) | 2005-10-05 |
JP2006516275A (ja) | 2006-06-29 |
EP1592661A2 (en) | 2005-11-09 |
IL169488A0 (en) | 2007-07-04 |
AU2004205523A1 (en) | 2004-08-05 |
US20040147608A1 (en) | 2004-07-29 |
KR100743800B1 (ko) | 2007-07-30 |
RU2005123305A (ru) | 2006-01-27 |
MXPA05007772A (es) | 2005-09-30 |
KR20050094452A (ko) | 2005-09-27 |
BRPI0406811A (pt) | 2005-12-27 |
US7030267B2 (en) | 2006-04-18 |
PL377937A1 (pl) | 2006-02-20 |
CN1764634A (zh) | 2006-04-26 |
NO20053408D0 (no) | 2005-07-13 |
RU2312853C2 (ru) | 2007-12-20 |
WO2004065361A3 (en) | 2004-10-07 |
CA2513150A1 (en) | 2004-08-05 |
WO2004065361A2 (en) | 2004-08-05 |
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