RU96111003A - DERIVATIVES N-ACYL-2-ARYLCYCLOPROPYLMETYLAMINE, STIMULATING MELATONIN SYNTHESIS, PHARMACEUTICAL COMPOSITION, RADIOLIGAND AND METHOD OF TREATMENT - Google Patents
DERIVATIVES N-ACYL-2-ARYLCYCLOPROPYLMETYLAMINE, STIMULATING MELATONIN SYNTHESIS, PHARMACEUTICAL COMPOSITION, RADIOLIGAND AND METHOD OF TREATMENTInfo
- Publication number
- RU96111003A RU96111003A RU96111003/04A RU96111003A RU96111003A RU 96111003 A RU96111003 A RU 96111003A RU 96111003/04 A RU96111003/04 A RU 96111003/04A RU 96111003 A RU96111003 A RU 96111003A RU 96111003 A RU96111003 A RU 96111003A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- trans
- butanamide
- cyclopropyl
- methoxyphenyl
- Prior art date
Links
- 239000002287 radioligand Substances 0.000 title claims 3
- 229960003987 Melatonin Drugs 0.000 title claims 2
- 230000015572 biosynthetic process Effects 0.000 title claims 2
- DRLFMBDRBRZALE-UHFFFAOYSA-N melatonin Chemical compound COC1=CC=C2NC=C(CCNC(C)=O)C2=C1 DRLFMBDRBRZALE-UHFFFAOYSA-N 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 230000004936 stimulating Effects 0.000 title claims 2
- 238000003786 synthesis reaction Methods 0.000 title claims 2
- 230000002194 synthesizing Effects 0.000 title claims 2
- 150000001875 compounds Chemical class 0.000 claims 21
- 239000001257 hydrogen Chemical group 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 150000002431 hydrogen Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- DNSISZSEWVHGLH-UHFFFAOYSA-N Butyramide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical group 0.000 claims 5
- UHKDUQGFWCOYBS-JSGCOSHPSA-N N-[[(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OC)=C1 UHKDUQGFWCOYBS-JSGCOSHPSA-N 0.000 claims 4
- STQYRZJRRDQZBX-AAEUAGOBSA-N N-[[(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methyl]propanamide Chemical compound CCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OC)=C1 STQYRZJRRDQZBX-AAEUAGOBSA-N 0.000 claims 3
- LZLJNOIJPPNEKM-RYUDHWBXSA-N N-[[(1R,2R)-2-(4-chloro-3-methoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=C(Cl)C(OC)=C1 LZLJNOIJPPNEKM-RYUDHWBXSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- -1 ethoxyphenyl Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 230000027288 circadian rhythm Effects 0.000 claims 2
- 230000035591 circadian rhythms Effects 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QTGPTRFPAUPZQG-OCCSQVGLSA-N 1-ethyl-3-[(1S,3R)-3-(3-methoxyphenyl)cyclohexyl]urea Chemical compound C1[C@@H](NC(=O)NCC)CCC[C@H]1C1=CC=CC(OC)=C1 QTGPTRFPAUPZQG-OCCSQVGLSA-N 0.000 claims 1
- UVTKKQFKSZYYBT-CMPLNLGQSA-N C(CCC)(=O)NC[C@H]1[C@@H](C1)C1=C(C(=CC=C1)OC)I Chemical compound C(CCC)(=O)NC[C@H]1[C@@H](C1)C1=C(C(=CC=C1)OC)I UVTKKQFKSZYYBT-CMPLNLGQSA-N 0.000 claims 1
- JWJCYKFZZODONL-HIFRSBDPSA-N N-[(1S,3R)-3-(3-methoxyphenyl)cyclohexyl]-2-methylpropanamide Chemical compound COC1=CC=CC([C@H]2C[C@H](CCC2)NC(=O)C(C)C)=C1 JWJCYKFZZODONL-HIFRSBDPSA-N 0.000 claims 1
- LETVMMVRWWYAMA-OCCSQVGLSA-N N-[(1S,3R)-3-(3-methoxyphenyl)cyclohexyl]acetamide Chemical compound COC1=CC=CC([C@H]2C[C@H](CCC2)NC(C)=O)=C1 LETVMMVRWWYAMA-OCCSQVGLSA-N 0.000 claims 1
- BFHHAOPFTDYOHR-HIFRSBDPSA-N N-[(1S,3R)-3-(3-methoxyphenyl)cyclohexyl]butanamide Chemical compound C1[C@@H](NC(=O)CCC)CCC[C@H]1C1=CC=CC(OC)=C1 BFHHAOPFTDYOHR-HIFRSBDPSA-N 0.000 claims 1
- NPUAXXPPAWPSQO-VHSXEESVSA-N N-[[(1R,2R)-2-(2,4-dibromo-5-methoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC(OC)=C(Br)C=C1Br NPUAXXPPAWPSQO-VHSXEESVSA-N 0.000 claims 1
- OJEQHYORUHOCEM-GXSJLCMTSA-N N-[[(1R,2R)-2-(2,5-difluorophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC(F)=CC=C1F OJEQHYORUHOCEM-GXSJLCMTSA-N 0.000 claims 1
- GGHDXHOQLDJOCG-GXSJLCMTSA-N N-[[(1R,2R)-2-(2-bromo-5-fluorophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC(F)=CC=C1Br GGHDXHOQLDJOCG-GXSJLCMTSA-N 0.000 claims 1
- VKVCBWDGPHRYIE-PWKISDLSSA-N N-[[(1R,2R)-2-(2-decan-3-yloxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCCCC(CC)OC1=CC=CC=C1[C@H]1[C@H](CNC(=O)CCC)C1 VKVCBWDGPHRYIE-PWKISDLSSA-N 0.000 claims 1
- OYYKQTCTZHWFFP-RRUPDEEPSA-N N-[[(1R,2R)-2-(2-dodecan-3-yloxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCCCCCC(CC)OC1=CC=CC=C1[C@H]1[C@H](CNC(=O)CCC)C1 OYYKQTCTZHWFFP-RRUPDEEPSA-N 0.000 claims 1
- RMYISNXLVMNDPG-CMPLNLGQSA-N N-[[(1R,2R)-2-(2-iodo-5-methoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC(OC)=CC=C1I RMYISNXLVMNDPG-CMPLNLGQSA-N 0.000 claims 1
- GNAPQQVTSUYQJT-NKUTVCTDSA-N N-[[(1R,2R)-2-(2-octan-3-yloxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCC(CC)OC1=CC=CC=C1[C@H]1[C@H](CNC(=O)CCC)C1 GNAPQQVTSUYQJT-NKUTVCTDSA-N 0.000 claims 1
- XBJWYICKAQHXGJ-AXUWQRLWSA-N N-[[(1R,2R)-2-(2-undecan-3-yloxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCCCCC(CC)OC1=CC=CC=C1[C@H]1[C@H](CNC(=O)CCC)C1 XBJWYICKAQHXGJ-AXUWQRLWSA-N 0.000 claims 1
- VZIGQPTVFPCAMW-AAEUAGOBSA-N N-[[(1R,2R)-2-(3-bromophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(Br)=C1 VZIGQPTVFPCAMW-AAEUAGOBSA-N 0.000 claims 1
- GUYVNOYQYXSNSG-AAEUAGOBSA-N N-[[(1R,2R)-2-(3-chlorophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(Cl)=C1 GUYVNOYQYXSNSG-AAEUAGOBSA-N 0.000 claims 1
- AERVKLMMJNBJDO-AAEUAGOBSA-N N-[[(1R,2R)-2-(3-fluorophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(F)=C1 AERVKLMMJNBJDO-AAEUAGOBSA-N 0.000 claims 1
- AEZUZAGTTLQGGI-ICSRJNTNSA-N N-[[(1R,2R)-2-(3-heptoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCCCOC1=CC=CC([C@H]2[C@@H](C2)CNC(=O)CCC)=C1 AEZUZAGTTLQGGI-ICSRJNTNSA-N 0.000 claims 1
- WELAZXGMZZNWFP-JSGCOSHPSA-N N-[[(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methyl]-2-methylpropanamide Chemical compound COC1=CC=CC([C@H]2[C@@H](C2)CNC(=O)C(C)C)=C1 WELAZXGMZZNWFP-JSGCOSHPSA-N 0.000 claims 1
- JXMIGZBMNNLGOQ-AAEUAGOBSA-N N-[[(1R,2R)-2-(3-methoxyphenyl)cyclopropyl]methyl]acetamide Chemical compound COC1=CC=CC([C@H]2[C@@H](C2)CNC(C)=O)=C1 JXMIGZBMNNLGOQ-AAEUAGOBSA-N 0.000 claims 1
- LMXXPVMKOOTGAB-KBPBESRZSA-N N-[[(1R,2R)-2-(3-methylphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(C)=C1 LMXXPVMKOOTGAB-KBPBESRZSA-N 0.000 claims 1
- NGGYMRHERMZKLI-UNMCSNQZSA-N N-[[(1R,2R)-2-(3-nonoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCCCCCCCOC1=CC=CC([C@H]2[C@@H](C2)CNC(=O)CCC)=C1 NGGYMRHERMZKLI-UNMCSNQZSA-N 0.000 claims 1
- IDIUZPZKUSXHHU-HOCLYGCPSA-N N-[[(1R,2R)-2-(3-prop-2-enoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OCC=C)=C1 IDIUZPZKUSXHHU-HOCLYGCPSA-N 0.000 claims 1
- BAWZUDYKKUVGDK-RYUDHWBXSA-N N-[[(1R,2R)-2-(4-iodo-3-methoxyphenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=C(I)C(OC)=C1 BAWZUDYKKUVGDK-RYUDHWBXSA-N 0.000 claims 1
- WYYFHDCJTGSIMC-GXSJLCMTSA-N N-[[(1R,2R)-2-(5-fluoro-2-iodophenyl)cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC(F)=CC=C1I WYYFHDCJTGSIMC-GXSJLCMTSA-N 0.000 claims 1
- DANHJPTVZWLPRP-FPOVZHCZSA-N N-[[(1R,2R)-2-[3-(2-phenylethoxy)phenyl]cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OCCC=2C=CC=CC=2)=C1 DANHJPTVZWLPRP-FPOVZHCZSA-N 0.000 claims 1
- OAEDZSSVQAUOFZ-AHWVRZQESA-N N-[[(1R,2R)-2-[3-(7-phenylheptoxy)phenyl]cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OCCCCCCCC=2C=CC=CC=2)=C1 OAEDZSSVQAUOFZ-AHWVRZQESA-N 0.000 claims 1
- BDRPTHLBJIXMOT-REWPJTCUSA-N N-[[(1R,2R)-2-[3-[3-(3-methoxyphenyl)propoxy]phenyl]cyclopropyl]methyl]butanamide Chemical compound CCCC(=O)NC[C@@H]1C[C@H]1C1=CC=CC(OCCCC=2C=C(OC)C=CC=2)=C1 BDRPTHLBJIXMOT-REWPJTCUSA-N 0.000 claims 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N Propadiene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N Propanamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
Claims (21)
в которой X - галоген, водород, С1-4алкил или OR5, где R5 представляет собой водород, С1-4перфторалкил, С1-4фторалкил, С1-4пердейтероалкил, С1-20алкил, С4-20алкциклоалкил, С2-20карбонитрилоалкил, С3-22карбоалкоксиалкил, С3-20алкенил, С3-20алкинил, С9-20аралкил, С9-20аралкенил, С9-20аралкинил, С2-20гидроксиалкил, С8-20арилоксиалкил, С7-20пиридилалкил или С6-20пиррилалкил; Y-водород или галоген; Z-водород, галоген, циано, арил, С7-20аралкил, С8-20аралкинил или С2-20алкамидо; R в обоих случаях является водородом, галогеном или С1-4алкилом; G - двухвалентный метилен, этилен или С1-4алкметиленовый фрагмент; R1 - водород, С1-4алкил или бензил; R2 - С1-6алкил, С2-6алкенил, С3-6циклоалкил, С2-4алкоксиалкил, С1-4трифторметилалкил, С2-8алкилтиоалкил или NR3R4, где R3 и R4 независимо друг от друга выбирают из водорода и С1-4алкила, но R3 и R4 не могут одновременно быть водородом.1. Derivatives of N-acyl-2-arylcyclopropylmethylamine of formula 1 or 11, stimulating the synthesis of melatonin:
in which X is halogen, hydrogen, C 1-4 alkyl or OR 5 , where R 5 is hydrogen, C 1-4 perfluoroalkyl, C 1-4 fluoroalkyl, C 1-4 perdeuteroalkyl, C 1-20 alkyl, C 4 -20 alkcycloalkyl, C 2-20 carbonitriloalkyl, C 3-22 carboalkoxyalkyl, C 3-20 alkenyl, C 3-20 alkynyl, C 9-20 aralkyl, C 9-20 aralkenyl, C 9-20 aralkynyl, C 2-20 hydroxyalkyl, C 8-20 aryloxyalkyl, C 7-20 pyridylalkyl or C 6-20 pyrrylalkyl; Y is hydrogen or halogen; Z-hydrogen, halogen, cyano, aryl, C 7-20 aralkyl, C 8-20 aralkynyl or C 2-20 alkamido; R in both cases is hydrogen, halogen or C 1-4 alkyl; G is a bivalent methylene, ethylene or C 1-4 alkmethylene fragment; R 1 is hydrogen, C 1-4 alkyl or benzyl; R 2 - C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, C 2-4 alkoxyalkyl, C 1-4 trifluoromethylalkyl, C 2-8 alkylthioalkyl or NR 3 R 4 where R 3 and R 4 are independently selected from hydrogen and C 1-4 alkyl, but R 3 and R 4 cannot simultaneously be hydrogen.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US48663395A | 1995-06-07 | 1995-06-07 | |
US486,633 | 1995-06-07 | ||
US08/487,306 US5596019A (en) | 1995-06-07 | 1995-06-07 | N-acyl-cycloalkylamine derivatives as melatonergics |
US487,306 | 1995-06-07 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU96111003A true RU96111003A (en) | 1998-09-27 |
RU2162076C2 RU2162076C2 (en) | 2001-01-20 |
Family
ID=27048750
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU96111003/04A RU2162076C2 (en) | 1995-06-07 | 1996-06-06 | Derivatives of n-acyl-2-arylcycloalkylamine stimulating melatonin synthesis, pharmaceutical composition, method of melatonin-stimulating binding |
Country Status (23)
Country | Link |
---|---|
EP (1) | EP0747346B1 (en) |
JP (1) | JPH08333314A (en) |
KR (1) | KR100385360B1 (en) |
CN (1) | CN1068583C (en) |
AR (1) | AR003139A1 (en) |
AT (1) | ATE189807T1 (en) |
AU (1) | AU697028B2 (en) |
CA (1) | CA2176854A1 (en) |
CY (1) | CY2221B1 (en) |
CZ (1) | CZ291380B6 (en) |
DE (1) | DE69606665T2 (en) |
DK (1) | DK0747346T3 (en) |
ES (1) | ES2144666T3 (en) |
GR (1) | GR3033414T3 (en) |
HK (1) | HK1014704A1 (en) |
HU (1) | HUP9601565A3 (en) |
IL (1) | IL118427A (en) |
NO (1) | NO311211B1 (en) |
NZ (1) | NZ286640A (en) |
PL (1) | PL314671A1 (en) |
PT (1) | PT747346E (en) |
RU (1) | RU2162076C2 (en) |
TW (1) | TW350836B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US8030337B2 (en) | 2006-06-19 | 2011-10-04 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
Families Citing this family (14)
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US5856529A (en) * | 1996-12-10 | 1999-01-05 | Bristol-Myers Squibb Company | Benzofuran and dihydrobenzofuran melatonergic agents |
US6028112A (en) * | 1997-05-23 | 2000-02-22 | Bristol-Myers Squibb Company | Spirocyclopropyl fluorenes as melatonergic agents |
US6214869B1 (en) * | 1998-06-05 | 2001-04-10 | Bristol-Myers Squibb | Heterocyclic cis cyclopropane derivatives as melatonergic agents |
WO2000000459A1 (en) * | 1998-06-29 | 2000-01-06 | Mitsubishi-Tokyo Pharmaceuticals, Inc. | Process for the preparation of optically active trans-cyclohexylamine compounds |
FR2784375B1 (en) * | 1998-10-12 | 2000-11-24 | Adir | NOVEL CYCLOALKYLENIC CHAIN DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
WO2000021910A2 (en) * | 1998-10-14 | 2000-04-20 | Ortho-Mcneil Pharmaceutical, Inc. | 1,2-disubstituted cyclopropanes |
PE20020665A1 (en) * | 2000-06-15 | 2002-08-14 | Pharmacia Corp | CYCLOALKYL PHENYL ALCANOIC ACID AS ANTAGONIST OF INTEGRINS OVß3 |
US7541055B2 (en) * | 2004-09-10 | 2009-06-02 | International Flavors & Fragrances Inc. | Saturated and unsaturated N-alkamides exhibiting taste and flavor enhancement effect in flavor compositions |
WO2007025144A1 (en) * | 2005-08-24 | 2007-03-01 | University Of Illinois - Chicago | 5-ht2c receptor agonists as anorectic agents |
US8835472B2 (en) * | 2010-09-02 | 2014-09-16 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical compositions and uses thereof |
MX2014014010A (en) * | 2012-05-18 | 2015-02-12 | Vanda Pharmaceuticals Inc | Metabolites of (1r-trans)-n-[[2-(2,3-dihydro-4-benzofuranyl)cyclo propyl]methyl]propanamide. |
CN102863341B (en) * | 2012-10-22 | 2014-05-07 | 南通大学 | Chemical synthesis method of (1R, 2S)-2-aryl cyclopropylamine derivative |
WO2016123164A1 (en) * | 2015-01-29 | 2016-08-04 | The Board Of Trustees Of The University Of Illinois | Cyclopropylmethanamines as selective 5-ht(2c) receptor agonists |
CN105949153B (en) * | 2016-05-10 | 2018-03-02 | 浙江工业大学 | A kind of Ta Simeiqiong synthetic method |
Family Cites Families (6)
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FR1415997A (en) * | 1963-11-05 | 1965-10-29 | Whitefin Holding Sa | Phenylcyclopropane derivatives and methods of preparation |
US5071875A (en) * | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
JP3007138B2 (en) * | 1990-11-27 | 2000-02-07 | ファイザー製薬株式会社 | Novel hydroxamic acid and N-hydroxyurea derivatives and compositions thereof |
FR2680366B1 (en) * | 1991-08-13 | 1995-01-20 | Adir | NOVEL ARYLETHYLAMINE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM. |
JP3333510B2 (en) * | 1991-10-02 | 2002-10-15 | スミスクライン・ビーチャム・コーポレイション | Cyclopentane and cyclopentene derivatives having antiallergic, antiinflammatory and tumor necrosis factor inhibitory activities |
US5541228A (en) * | 1994-10-14 | 1996-07-30 | Bristol-Myers Squibb Co. | Melatonergic agents |
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1996
- 1996-05-17 CA CA002176854A patent/CA2176854A1/en not_active Abandoned
- 1996-05-22 NZ NZ286640A patent/NZ286640A/en unknown
- 1996-05-23 TW TW085106143A patent/TW350836B/en active
- 1996-05-27 IL IL11842796A patent/IL118427A/en not_active IP Right Cessation
- 1996-05-31 ES ES96108764T patent/ES2144666T3/en not_active Expired - Lifetime
- 1996-05-31 EP EP96108764A patent/EP0747346B1/en not_active Expired - Lifetime
- 1996-05-31 DE DE69606665T patent/DE69606665T2/en not_active Expired - Fee Related
- 1996-05-31 PT PT96108764T patent/PT747346E/en unknown
- 1996-05-31 AT AT96108764T patent/ATE189807T1/en not_active IP Right Cessation
- 1996-05-31 DK DK96108764T patent/DK0747346T3/en active
- 1996-06-05 CZ CZ19961631A patent/CZ291380B6/en not_active IP Right Cessation
- 1996-06-06 NO NO19962364A patent/NO311211B1/en not_active IP Right Cessation
- 1996-06-06 RU RU96111003/04A patent/RU2162076C2/en not_active IP Right Cessation
- 1996-06-06 AU AU54759/96A patent/AU697028B2/en not_active Ceased
- 1996-06-06 HU HU9601565A patent/HUP9601565A3/en unknown
- 1996-06-06 JP JP8144018A patent/JPH08333314A/en active Pending
- 1996-06-07 KR KR1019960020713A patent/KR100385360B1/en not_active IP Right Cessation
- 1996-06-07 AR ARP960103052A patent/AR003139A1/en not_active Application Discontinuation
- 1996-06-07 CN CN96108134A patent/CN1068583C/en not_active Expired - Fee Related
- 1996-06-07 PL PL96314671A patent/PL314671A1/en unknown
-
1998
- 1998-12-28 HK HK98116041A patent/HK1014704A1/en not_active IP Right Cessation
-
2000
- 2000-05-15 GR GR20000401104T patent/GR3033414T3/en not_active IP Right Cessation
-
2001
- 2001-05-04 CY CY0100007A patent/CY2221B1/en unknown
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8030337B2 (en) | 2006-06-19 | 2011-10-04 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8236837B2 (en) | 2006-06-19 | 2012-08-07 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8349879B2 (en) | 2006-06-19 | 2013-01-08 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8552037B2 (en) | 2006-06-19 | 2013-10-08 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
US8895591B2 (en) | 2006-06-19 | 2014-11-25 | Takeda Pharmaceutical Company Limited | Tricyclic compound and pharmaceutical use thereof |
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