JP2003518136A - 新規な化合物 - Google Patents
新規な化合物Info
- Publication number
- JP2003518136A JP2003518136A JP2001547172A JP2001547172A JP2003518136A JP 2003518136 A JP2003518136 A JP 2003518136A JP 2001547172 A JP2001547172 A JP 2001547172A JP 2001547172 A JP2001547172 A JP 2001547172A JP 2003518136 A JP2003518136 A JP 2003518136A
- Authority
- JP
- Japan
- Prior art keywords
- piperidinyl
- amino
- benzamide
- diethyl
- hydroxyphenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 12
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 12
- 125000002346 iodo group Chemical group I* 0.000 claims abstract description 12
- 125000001424 substituent group Chemical group 0.000 claims abstract description 12
- 208000002193 Pain Diseases 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 230000036407 pain Effects 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract description 5
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 5
- 125000001425 triazolyl group Chemical group 0.000 claims abstract description 5
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract 3
- 239000000126 substance Substances 0.000 claims description 53
- 238000000034 method Methods 0.000 claims description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 208000020431 spinal cord injury Diseases 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- PWAHBRNWPAQLDU-UHFFFAOYSA-N 4-(n-(1-benzylpiperidin-4-yl)-5-hydroxy-2-iodoanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C(=CC=C(O)C=1)I)C1CCN(CC=2C=CC=CC=2)CC1 PWAHBRNWPAQLDU-UHFFFAOYSA-N 0.000 claims description 3
- ZNUIIBUGODHZMS-UHFFFAOYSA-N 4-(n-(1-benzylpiperidin-4-yl)-2-bromo-5-hydroxyanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C(=CC=C(O)C=1)Br)C1CCN(CC=2C=CC=CC=2)CC1 ZNUIIBUGODHZMS-UHFFFAOYSA-N 0.000 claims description 2
- ZLTZCMNKTGITGP-UHFFFAOYSA-N 4-(n-(1-benzylpiperidin-4-yl)-2-fluoro-5-hydroxyanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C(=CC=C(O)C=1)F)C1CCN(CC=2C=CC=CC=2)CC1 ZLTZCMNKTGITGP-UHFFFAOYSA-N 0.000 claims description 2
- SRFARMYXBYDWBL-UHFFFAOYSA-N 4-(n-[1-[(4-chlorophenyl)methyl]piperidin-4-yl]-3-hydroxyanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC=2C=CC(Cl)=CC=2)CC1 SRFARMYXBYDWBL-UHFFFAOYSA-N 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- DBDFCAIWUBMWBJ-UHFFFAOYSA-N n,n-diethyl-4-(3-hydroxy-n-[1-(thiophen-3-ylmethyl)piperidin-4-yl]anilino)benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC2=CSC=C2)CC1 DBDFCAIWUBMWBJ-UHFFFAOYSA-N 0.000 claims description 2
- DMEADXCOOZTKBV-UHFFFAOYSA-N n,n-diethyl-4-(n-[1-[(4-fluorophenyl)methyl]piperidin-4-yl]-3-hydroxyanilino)benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC=2C=CC(F)=CC=2)CC1 DMEADXCOOZTKBV-UHFFFAOYSA-N 0.000 claims description 2
- 210000002820 sympathetic nervous system Anatomy 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- BWLIJEAKIOLWFP-UHFFFAOYSA-N 4-(n-(1-benzylpiperidin-4-yl)-2-chloro-5-hydroxyanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C(=CC=C(O)C=1)Cl)C1CCN(CC=2C=CC=CC=2)CC1 BWLIJEAKIOLWFP-UHFFFAOYSA-N 0.000 claims 1
- WILATYUMLLLBFE-UHFFFAOYSA-N 4-(n-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-3-hydroxyanilino)-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC=2C(=CC(Cl)=CC=2)Cl)CC1 WILATYUMLLLBFE-UHFFFAOYSA-N 0.000 claims 1
- RBFDCFLNWXKHFK-UHFFFAOYSA-N C(C)N(C(C1=CC=C(C=C1)N(C1=CC(=CC=C1)O)C1CCN(CC1)CC1=CC=C(C=C1)Br)=O)CC.C(C)N(C(C1=CC=C(C=C1)N(C1CCN(CC1)CC1=CC=C(C=C1)I)C1=CC(=CC=C1)O)=O)CC Chemical compound C(C)N(C(C1=CC=C(C=C1)N(C1=CC(=CC=C1)O)C1CCN(CC1)CC1=CC=C(C=C1)Br)=O)CC.C(C)N(C(C1=CC=C(C=C1)N(C1CCN(CC1)CC1=CC=C(C=C1)I)C1=CC(=CC=C1)O)=O)CC RBFDCFLNWXKHFK-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 claims 1
- 208000019423 liver disease Diseases 0.000 claims 1
- GMVFOJKDXATNNM-UHFFFAOYSA-N n,n-diethyl-4-(3-hydroxy-n-[1-[(4-methylphenyl)methyl]piperidin-4-yl]anilino)benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC=2C=CC(C)=CC=2)CC1 GMVFOJKDXATNNM-UHFFFAOYSA-N 0.000 claims 1
- MPFKAGVQJDJAAD-UHFFFAOYSA-N n,n-diethyl-4-(n-[1-(furan-3-ylmethyl)piperidin-4-yl]-3-hydroxyanilino)benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(O)C=CC=1)C1CCN(CC2=COC=C2)CC1 MPFKAGVQJDJAAD-UHFFFAOYSA-N 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 description 44
- 238000004128 high performance liquid chromatography Methods 0.000 description 33
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- -1 dioxane Compound Chemical class 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000012360 testing method Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000009870 specific binding Effects 0.000 description 12
- 230000004044 response Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002287 radioligand Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 210000004209 hair Anatomy 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 108700023159 delta Opioid Receptors Proteins 0.000 description 5
- 102000048124 delta Opioid Receptors Human genes 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000003840 hydrochlorides Chemical class 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- VVAIWOCQSIZXMI-UHFFFAOYSA-N 4-[n-(1-benzylpiperidin-4-yl)-2-bromo-5-[tert-butyl(dimethyl)silyl]oxyanilino]-n,n-diethylbenzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C(=CC=C(O[Si](C)(C)C(C)(C)C)C=1)Br)C1CCN(CC=2C=CC=CC=2)CC1 VVAIWOCQSIZXMI-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000841 delta opiate receptor agonist Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- NYQMISWQRDTXSS-UHFFFAOYSA-N n,n-diethyl-4-(3-methoxy-n-piperidin-4-ylanilino)benzamide Chemical compound C1=CC(C(=O)N(CC)CC)=CC=C1N(C=1C=C(OC)C=CC=1)C1CCNCC1 NYQMISWQRDTXSS-UHFFFAOYSA-N 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 2
- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 2
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 2
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 2
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9904675-7 | 1999-12-20 | ||
| SE9904675A SE9904675D0 (sv) | 1999-12-20 | 1999-12-20 | Novel compounds |
| PCT/SE2000/002560 WO2001046263A1 (en) | 1999-12-20 | 2000-12-15 | Novel compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003518136A true JP2003518136A (ja) | 2003-06-03 |
| JP2003518136A5 JP2003518136A5 (enExample) | 2008-02-07 |
Family
ID=20418211
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001547172A Abandoned JP2003518136A (ja) | 1999-12-20 | 2000-12-15 | 新規な化合物 |
Country Status (32)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE0101770D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101771D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| SE0101773D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| NZ539828A (en) | 2001-05-18 | 2007-01-26 | Astrazeneca Ab | 4 (phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders |
| SE0101769D0 (sv) * | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
| JP4892654B2 (ja) * | 2001-10-29 | 2012-03-07 | マウント クック ファーマ，インコーポレーテッド | デルタレセプターアゴニスト化合物によるうつ病の治療方法 |
| PL372096A1 (en) | 2002-01-02 | 2005-07-11 | Ardent Pharmaceuticals, Inc. | Method of treating sexual dysfunctions with delta opioid receptor agonist compounds |
| US8476280B2 (en) * | 2002-05-09 | 2013-07-02 | Versi Group, Llc | Compositions and methods for combating lower urinary tract dysfunctions with delta opioid receptor agonists |
| SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| KR101234421B1 (ko) | 2004-08-02 | 2013-02-18 | 아스트라제네카 아베 | 디아릴메틸 피페라진 유도체, 이의 제조 방법 및 용도 |
| CN101128447A (zh) * | 2005-02-28 | 2008-02-20 | 阿斯利康(瑞典)有限公司 | 二芳基甲基哌嗪衍生物，其制备及其用途 |
| US20250084091A1 (en) * | 2021-05-04 | 2025-03-13 | The Texas A&M University System | Inhibitors of sars-cov-2 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091096A (en) | 1976-03-19 | 1978-05-23 | Eli Lilly And Company | Dinitroanilines for the control of phytopathogens |
| EG12406A (en) | 1976-08-12 | 1979-03-31 | Janssen Pharmaceutica Nv | Process for preparing of novel n-aryl-n-(1-l-4-piperidinyl)-arylacetamides |
| SE441448B (sv) | 1977-05-23 | 1985-10-07 | Pfizer | Sett att framstella hexahydro-gamma-karbolinforeningar |
| DE3200304A1 (de) | 1981-01-16 | 1982-08-26 | Sandoz-Patent-GmbH, 7850 Lörrach | 3-aminopropoxyaryl-derivate, ihre herstellung und sie enthaltende arzneimittel |
| DE3563964D1 (en) | 1984-10-16 | 1988-09-01 | Synthelabo | Piperidine derivatives, their preparation and their therapeutical application |
| KR940003491B1 (ko) | 1989-08-10 | 1994-04-23 | 리히터 게데온 베기에스제티 기아르 알.티 | 4,4-이중 치환된 피페리딘 유도체와 그 제조방법 및 상기 화합물을 함유하는 약제학적 조성물 |
| YU150489A (sh) | 1989-08-10 | 1992-12-21 | W.L. Gore & Co. Gmbh. | Uređaj za ispitivanje odevnih predmeta na nepromočivost |
| US5854245A (en) | 1996-06-28 | 1998-12-29 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
| CA2316341A1 (en) * | 1997-12-24 | 1999-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | 4-[aryl(piperidin-4-yl)] aminobenzamides which bind to the delta-opioid receptor |
| JP4498602B2 (ja) * | 1998-03-10 | 2010-07-07 | リサーチ・トライアングル・インスティチュート | 新規なオピエート化合物、その調製法及び使用法 |
| US6436959B1 (en) * | 1998-12-23 | 2002-08-20 | Ortho-Mcneil Pharmaceutical, Inc. | 4-[aryl(piperidin-4-yl)]aminobenzamides |
-
1999
- 1999-12-20 SE SE9904675A patent/SE9904675D0/xx unknown
-
2000
- 2000-12-15 CZ CZ20022123A patent/CZ20022123A3/cs unknown
- 2000-12-15 ES ES00989097T patent/ES2215786T3/es not_active Expired - Lifetime
- 2000-12-15 EE EEP200200338A patent/EE200200338A/xx unknown
- 2000-12-15 SK SK884-2002A patent/SK8842002A3/sk unknown
- 2000-12-15 US US10/149,982 patent/US6875777B2/en not_active Expired - Fee Related
- 2000-12-15 KR KR1020027007837A patent/KR20020062351A/ko not_active Withdrawn
- 2000-12-15 AT AT00989097T patent/ATE261957T1/de not_active IP Right Cessation
- 2000-12-15 IL IL15021000A patent/IL150210A0/xx unknown
- 2000-12-15 HU HU0300295A patent/HUP0300295A3/hu unknown
- 2000-12-15 EP EP00989097A patent/EP1242406B1/en not_active Expired - Lifetime
- 2000-12-15 CN CNB00819064XA patent/CN1185227C/zh not_active Expired - Fee Related
- 2000-12-15 TR TR2004/01433T patent/TR200401433T4/xx unknown
- 2000-12-15 HK HK03100303.9A patent/HK1048629B/en not_active IP Right Cessation
- 2000-12-15 DK DK00989097T patent/DK1242406T3/da active
- 2000-12-15 AU AU25644/01A patent/AU775648B2/en not_active Ceased
- 2000-12-15 BR BR0016594-8A patent/BR0016594A/pt not_active IP Right Cessation
- 2000-12-15 NZ NZ519987A patent/NZ519987A/en unknown
- 2000-12-15 WO PCT/SE2000/002560 patent/WO2001046263A1/en not_active Ceased
- 2000-12-15 PT PT00989097T patent/PT1242406E/pt unknown
- 2000-12-15 UA UA2002064616A patent/UA72287C2/uk unknown
- 2000-12-15 RU RU2002114346/04A patent/RU2002114346A/ru not_active Application Discontinuation
- 2000-12-15 DE DE60009148T patent/DE60009148T2/de not_active Expired - Fee Related
- 2000-12-15 PL PL00355843A patent/PL355843A1/xx not_active Application Discontinuation
- 2000-12-15 CA CA002394864A patent/CA2394864A1/en not_active Abandoned
- 2000-12-15 JP JP2001547172A patent/JP2003518136A/ja not_active Abandoned
- 2000-12-15 MX MXPA02006064A patent/MXPA02006064A/es active IP Right Grant
- 2000-12-19 CO CO00096315A patent/CO5271645A1/es not_active Application Discontinuation
-
2002
- 2002-05-28 ZA ZA200204257A patent/ZA200204257B/en unknown
- 2002-06-10 BG BG106807A patent/BG106807A/xx unknown
- 2002-06-12 IS IS6419A patent/IS6419A/is unknown
- 2002-06-18 NO NO20022919A patent/NO20022919L/no not_active Application Discontinuation
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