TW200418799A - Phenyl or heteroaryl amino alkane derivatives - Google Patents
Phenyl or heteroaryl amino alkane derivatives Download PDFInfo
- Publication number
- TW200418799A TW200418799A TW092131351A TW92131351A TW200418799A TW 200418799 A TW200418799 A TW 200418799A TW 092131351 A TW092131351 A TW 092131351A TW 92131351 A TW92131351 A TW 92131351A TW 200418799 A TW200418799 A TW 200418799A
- Authority
- TW
- Taiwan
- Prior art keywords
- group
- phenyl
- substituted
- alkyl
- mono
- Prior art date
Links
- -1 heteroaryl amino alkane Chemical class 0.000 title claims abstract description 371
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims abstract description 252
- 150000001875 compounds Chemical class 0.000 claims abstract description 162
- 108091006335 Prostaglandin I receptors Proteins 0.000 claims abstract description 27
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 208000002193 Pain Diseases 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 239000004480 active ingredient Substances 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 10
- 208000014001 urinary system disease Diseases 0.000 claims abstract description 10
- 208000001953 Hypotension Diseases 0.000 claims abstract description 8
- 206010061218 Inflammation Diseases 0.000 claims abstract description 8
- 230000036543 hypotension Effects 0.000 claims abstract description 8
- 230000004054 inflammatory process Effects 0.000 claims abstract description 8
- 239000002464 receptor antagonist Substances 0.000 claims abstract description 8
- 229940044551 receptor antagonist Drugs 0.000 claims abstract description 8
- 208000032843 Hemorrhage Diseases 0.000 claims abstract description 7
- 208000031220 Hemophilia Diseases 0.000 claims abstract description 6
- 208000009292 Hemophilia A Diseases 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- 230000002079 cooperative effect Effects 0.000 claims description 95
- 125000003545 alkoxy group Chemical group 0.000 claims description 89
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 80
- 229910052739 hydrogen Inorganic materials 0.000 claims description 80
- 125000003282 alkyl amino group Chemical group 0.000 claims description 77
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 54
- 150000001412 amines Chemical class 0.000 claims description 53
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
- 229920006395 saturated elastomer Polymers 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 43
- 125000002837 carbocyclic group Chemical group 0.000 claims description 43
- 125000001624 naphthyl group Chemical group 0.000 claims description 43
- 125000005843 halogen group Chemical group 0.000 claims description 39
- 125000000304 alkynyl group Chemical group 0.000 claims description 38
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 37
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 35
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 34
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 33
- 125000001041 indolyl group Chemical group 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
- 125000004414 alkyl thio group Chemical group 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000003277 amino group Chemical group 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 23
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 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 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 235000004279 alanine Nutrition 0.000 claims description 20
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 18
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 17
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 16
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 11
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 10
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 10
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical group NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 9
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 claims description 9
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 claims description 9
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 claims description 9
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 8
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 claims description 8
- 150000003973 alkyl amines Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 238000007639 printing Methods 0.000 claims description 8
- 235000021286 stilbenes Nutrition 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 6
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 230000000740 bleeding effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 241000700159 Rattus Species 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 239000005557 antagonist Substances 0.000 claims description 4
- 208000034158 bleeding Diseases 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000007789 gas Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000004575 stone Chemical group 0.000 claims description 4
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 3
- 241000283074 Equus asinus Species 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002757 morpholinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000000109 phenylethoxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])O* 0.000 claims description 3
- 229960000948 quinine Drugs 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 108020003175 receptors Proteins 0.000 claims description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
- CDYAZGSXKBVOFC-DEOSSOPVSA-N (2s)-2-[[6-[4-[(3-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=CC=2)=CC=1)C1=CC=CC=C1 CDYAZGSXKBVOFC-DEOSSOPVSA-N 0.000 claims description 2
- PSXGSFPFCUSNHR-QHCPKHFHSA-N (2s)-2-[[6-[4-[(3-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=CC=2)=CC=1)C1=CC=CC=N1 PSXGSFPFCUSNHR-QHCPKHFHSA-N 0.000 claims description 2
- DIQYJMGQWDEHSP-NDEPHWFRSA-N (2s)-3-[3-[2-(dimethylamino)ethoxy]phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound CN(C)CCOC1=CC=CC(C[C@H](NC=2N=CN=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(O)=O)=C1 DIQYJMGQWDEHSP-NDEPHWFRSA-N 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000004175 fluorobenzyl group Chemical group 0.000 claims description 2
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 2
- BUIMWOLDCCGZKZ-UHFFFAOYSA-N n-hydroxynitramide Chemical group ON[N+]([O-])=O BUIMWOLDCCGZKZ-UHFFFAOYSA-N 0.000 claims description 2
- ZNPKAOCQMDJBIK-UHFFFAOYSA-N nitrocyanamide Chemical compound [O-][N+](=O)NC#N ZNPKAOCQMDJBIK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005630 sialyl group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- XMDBJQOQTPRRJM-UHFFFAOYSA-N 1-nitro-n-oxido-n-oxomethanimidamide Chemical group NC(=N)[N+]([O-])=O XMDBJQOQTPRRJM-UHFFFAOYSA-N 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- CNMAQBJBWQQZFZ-LURJTMIESA-N (2s)-2-(pyridin-2-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CC=N1 CNMAQBJBWQQZFZ-LURJTMIESA-N 0.000 claims 1
- PDSGMAQAFXECJJ-QHCPKHFHSA-N (2s)-2-[[6-(3-fluoro-4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=C(F)C(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 PDSGMAQAFXECJJ-QHCPKHFHSA-N 0.000 claims 1
- JEHSGHRHLCWGMV-DEOSSOPVSA-N (2s)-2-[[6-[4-(2-phenylethoxy)phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 JEHSGHRHLCWGMV-DEOSSOPVSA-N 0.000 claims 1
- NXLNNDZBYAPAOS-DEOSSOPVSA-N (2s)-2-[[6-[4-(3-methoxyphenyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(C=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 NXLNNDZBYAPAOS-DEOSSOPVSA-N 0.000 claims 1
- ITEUWUMKZSPMJB-DEOSSOPVSA-N (2s)-2-[[6-[4-[(3,5-difluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1)C1=CC=CC=C1 ITEUWUMKZSPMJB-DEOSSOPVSA-N 0.000 claims 1
- YRYPTCVIRZWGBQ-VWLOTQADSA-N (2s)-2-[[6-[4-[(3-methoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 YRYPTCVIRZWGBQ-VWLOTQADSA-N 0.000 claims 1
- YKOVOXGNQHYDLO-DEOSSOPVSA-N (2s)-2-[[6-[4-[(4-fluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC(F)=CC=2)=CC=1)C1=CC=CC=C1 YKOVOXGNQHYDLO-DEOSSOPVSA-N 0.000 claims 1
- PDRJLZDUOULRHE-ZETCQYMHSA-N (2s)-2-amino-3-pyridin-2-ylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=N1 PDRJLZDUOULRHE-ZETCQYMHSA-N 0.000 claims 1
- AFRDMVIWRZTGGG-NRFANRHFSA-N (2s)-3-(4-chlorophenyl)-2-[[6-[4-(cyclopropylmethoxy)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC2CC2)=CC=1)C1=CC=C(Cl)C=C1 AFRDMVIWRZTGGG-NRFANRHFSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 claims 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims 1
- XWHHYOYVRVGJJY-QMMMGPOBSA-N 4-fluoro-L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(F)C=C1 XWHHYOYVRVGJJY-QMMMGPOBSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 125000006323 alkenyl amino group Chemical group 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims 1
- 150000001602 bicycloalkyls Chemical group 0.000 claims 1
- 230000001276 controlling effect Effects 0.000 claims 1
- JKZWPSHYNAEPAA-UHFFFAOYSA-N cyanocarbamic acid Chemical group OC(=O)NC#N JKZWPSHYNAEPAA-UHFFFAOYSA-N 0.000 claims 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000005241 heteroarylamino group Chemical group 0.000 claims 1
- TZYZQIAHNRAIRQ-UHFFFAOYSA-N hydrazine stilbene Chemical compound NN.C1(=CC=CC=C1)C=CC1=CC=CC=C1 TZYZQIAHNRAIRQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- MKQLBNJQQZRQJU-UHFFFAOYSA-N morpholin-4-amine Chemical compound NN1CCOCC1 MKQLBNJQQZRQJU-UHFFFAOYSA-N 0.000 claims 1
- 125000005245 nitryl group Chemical group [N+](=O)([O-])* 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 230000001755 vocal effect Effects 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 abstract description 23
- 206010020853 Hypertonic bladder Diseases 0.000 abstract description 9
- 230000003042 antagnostic effect Effects 0.000 abstract description 9
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 abstract description 5
- 206010071445 Bladder outlet obstruction Diseases 0.000 abstract description 5
- 208000009722 Overactive Urinary Bladder Diseases 0.000 abstract description 5
- 208000004403 Prostatic Hyperplasia Diseases 0.000 abstract description 5
- 208000003800 Urinary Bladder Neck Obstruction Diseases 0.000 abstract description 5
- 208000020629 overactive bladder Diseases 0.000 abstract description 5
- 206010020751 Hypersensitivity Diseases 0.000 abstract description 4
- 208000012931 Urologic disease Diseases 0.000 abstract description 4
- 208000026935 allergic disease Diseases 0.000 abstract description 4
- 230000009610 hypersensitivity Effects 0.000 abstract description 4
- 206010036018 Pollakiuria Diseases 0.000 abstract description 3
- 206010046543 Urinary incontinence Diseases 0.000 abstract description 3
- 201000003146 cystitis Diseases 0.000 abstract description 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 3
- 230000036318 urination frequency Effects 0.000 abstract description 3
- 208000000094 Chronic Pain Diseases 0.000 abstract description 2
- 206010019233 Headaches Diseases 0.000 abstract description 2
- 206010065390 Inflammatory pain Diseases 0.000 abstract description 2
- 208000000450 Pelvic Pain Diseases 0.000 abstract description 2
- 208000005298 acute pain Diseases 0.000 abstract description 2
- 231100000869 headache Toxicity 0.000 abstract description 2
- 208000004296 neuralgia Diseases 0.000 abstract description 2
- 208000021722 neuropathic pain Diseases 0.000 abstract description 2
- 206010029446 nocturia Diseases 0.000 abstract description 2
- 201000007094 prostatitis Diseases 0.000 abstract description 2
- 208000011580 syndromic disease Diseases 0.000 abstract description 2
- 208000000143 urethritis Diseases 0.000 abstract description 2
- 208000022934 urinary frequency Diseases 0.000 abstract description 2
- 208000009935 visceral pain Diseases 0.000 abstract description 2
- 206010027566 Micturition urgency Diseases 0.000 abstract 1
- 206010065347 Premenstrual pain Diseases 0.000 abstract 1
- 206010036968 Prostatic pain Diseases 0.000 abstract 1
- 206010069645 Reduced bladder capacity Diseases 0.000 abstract 1
- 206010066218 Stress Urinary Incontinence Diseases 0.000 abstract 1
- 230000035874 hyperreactivity Effects 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 201000004240 prostatic hypertrophy Diseases 0.000 abstract 1
- 208000022170 stress incontinence Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 321
- 239000000203 mixture Substances 0.000 description 204
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 167
- 230000002829 reductive effect Effects 0.000 description 153
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 103
- 239000000243 solution Substances 0.000 description 103
- 238000006243 chemical reaction Methods 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 75
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 70
- 239000007787 solid Substances 0.000 description 61
- 229960005190 phenylalanine Drugs 0.000 description 57
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 54
- 238000012360 testing method Methods 0.000 description 53
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 235000008729 phenylalanine Nutrition 0.000 description 50
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- 239000012044 organic layer Substances 0.000 description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 47
- 239000012267 brine Substances 0.000 description 46
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 46
- 239000007864 aqueous solution Substances 0.000 description 44
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 43
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 43
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 42
- 230000000694 effects Effects 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 42
- 229910052938 sodium sulfate Inorganic materials 0.000 description 42
- 235000011152 sodium sulphate Nutrition 0.000 description 42
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 40
- 239000002585 base Substances 0.000 description 39
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 36
- 238000002844 melting Methods 0.000 description 34
- 230000008018 melting Effects 0.000 description 34
- 238000001816 cooling Methods 0.000 description 32
- 239000002904 solvent Substances 0.000 description 32
- 238000001914 filtration Methods 0.000 description 31
- 239000002244 precipitate Substances 0.000 description 31
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 31
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- 238000001819 mass spectrum Methods 0.000 description 29
- 239000011541 reaction mixture Substances 0.000 description 29
- 238000003756 stirring Methods 0.000 description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 27
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 238000004440 column chromatography Methods 0.000 description 26
- 238000012746 preparative thin layer chromatography Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 25
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 24
- 239000012043 crude product Substances 0.000 description 22
- 229910052763 palladium Inorganic materials 0.000 description 22
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 22
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 21
- 229910000027 potassium carbonate Inorganic materials 0.000 description 20
- 235000011181 potassium carbonates Nutrition 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000002431 hydrogen Chemical class 0.000 description 18
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- 101000862089 Clarkia lewisii Glucose-6-phosphate isomerase, cytosolic 1A Proteins 0.000 description 15
- 235000002639 sodium chloride Nutrition 0.000 description 15
- 150000002170 ethers Chemical class 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- KAQKFAOMNZTLHT-OZUDYXHBSA-N prostaglandin I2 Chemical compound O1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-OZUDYXHBSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- 150000001298 alcohols Chemical class 0.000 description 13
- 239000012230 colorless oil Substances 0.000 description 13
- VSDUZFOSJDMAFZ-VIFPVBQESA-N methyl L-phenylalaninate Chemical compound COC(=O)[C@@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-VIFPVBQESA-N 0.000 description 13
- 125000006239 protecting group Chemical group 0.000 description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 235000011118 potassium hydroxide Nutrition 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 229910000029 sodium carbonate Inorganic materials 0.000 description 10
- 235000017550 sodium carbonate Nutrition 0.000 description 10
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 9
- PKVRJCUKSNFIBN-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 PKVRJCUKSNFIBN-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- DMJHEIDWSIAXCS-UHFFFAOYSA-N (4-phenylmethoxyphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OCC1=CC=CC=C1 DMJHEIDWSIAXCS-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005909 Kieselgur Substances 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 230000008602 contraction Effects 0.000 description 6
- 150000008282 halocarbons Chemical class 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 230000001020 rhythmical effect Effects 0.000 description 6
- 210000001044 sensory neuron Anatomy 0.000 description 6
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 229940086542 triethylamine Drugs 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 239000001273 butane Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 150000003180 prostaglandins Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- OUHLAPXCAXDENW-QHCPKHFHSA-N (2s)-3-phenyl-2-[[2-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=C(N=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 OUHLAPXCAXDENW-QHCPKHFHSA-N 0.000 description 4
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 4
- XJPZKYIHCLDXST-UHFFFAOYSA-N 4,6-dichloropyrimidine Chemical compound ClC1=CC(Cl)=NC=N1 XJPZKYIHCLDXST-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 210000005069 ears Anatomy 0.000 description 4
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- PDRJLZDUOULRHE-SSDOTTSWSA-N (2r)-2-azaniumyl-3-pyridin-2-ylpropanoate Chemical compound OC(=O)[C@H](N)CC1=CC=CC=N1 PDRJLZDUOULRHE-SSDOTTSWSA-N 0.000 description 3
- JFARWEWTPMAQHW-DHZHZOJOSA-N (e)-3-(4-bromophenyl)-1-phenylprop-2-en-1-one Chemical compound C1=CC(Br)=CC=C1\C=C\C(=O)C1=CC=CC=C1 JFARWEWTPMAQHW-DHZHZOJOSA-N 0.000 description 3
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 208000004454 Hyperalgesia Diseases 0.000 description 3
- 208000035154 Hyperesthesia Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 102000003923 Protein Kinase C Human genes 0.000 description 3
- 108090000315 Protein Kinase C Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001409 amidines Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000006285 cell suspension Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- HBNBMOGARBJBHS-UHFFFAOYSA-N dimethylarsane Chemical compound C[AsH]C HBNBMOGARBJBHS-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- CJGXMNONHNZEQQ-JTQLQIEISA-N ethyl (2s)-2-amino-3-phenylpropanoate Chemical compound CCOC(=O)[C@@H](N)CC1=CC=CC=C1 CJGXMNONHNZEQQ-JTQLQIEISA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 210000004072 lung Anatomy 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VBUFNJYDRWAZIP-SFHVURJKSA-N methyl (2S)-2-[[6-(4-hydroxyphenyl)pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(O)=CC=1)C1=CC=CC=C1 VBUFNJYDRWAZIP-SFHVURJKSA-N 0.000 description 3
- FNKMBMZGRDAIGH-HNNXBMFYSA-N methyl (2s)-2-(3-bromoanilino)-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1C=C(Br)C=CC=1)C1=CC=CC=C1 FNKMBMZGRDAIGH-HNNXBMFYSA-N 0.000 description 3
- XCNYXPHPQBGOIV-NSHDSACASA-N methyl (2s)-2-[(6-chloropyrimidin-4-yl)amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(Cl)C=1)C1=CC=CC=C1 XCNYXPHPQBGOIV-NSHDSACASA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 239000008363 phosphate buffer Substances 0.000 description 3
- 235000015497 potassium bicarbonate Nutrition 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- UUZRNCDGBZOORO-MHZLTWQESA-N tert-butyl (2s)-3-phenyl-2-[[4-(4-phenylmethoxyphenyl)pyrimidin-2-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OC(C)(C)C)NC=1N=C(C=CN=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 UUZRNCDGBZOORO-MHZLTWQESA-N 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 210000001170 unmyelinated nerve fiber Anatomy 0.000 description 3
- 239000003039 volatile agent Substances 0.000 description 3
- GOGGNVOOSISWLB-QFIPXVFZSA-N (2s)-2-[[6-[4-(4-cyanopyridin-2-yl)oxyphenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OC=2N=CC=C(C=2)C#N)=CC=1)C1=CC=CC=C1 GOGGNVOOSISWLB-QFIPXVFZSA-N 0.000 description 2
- IYACDJYRATZDFJ-SANMLTNESA-N (2s)-3-phenyl-2-[[2-(4-phenylmethoxyphenyl)pyridin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C=C(N=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 IYACDJYRATZDFJ-SANMLTNESA-N 0.000 description 2
- CBGSRTIDTAZXIT-VWLOTQADSA-N (2s)-3-phenyl-2-[[6-[4-(2-phenylethynyl)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(=CC=1)C#CC=1C=CC=CC=1)C1=CC=CC=C1 CBGSRTIDTAZXIT-VWLOTQADSA-N 0.000 description 2
- MVOGOYDQONARRD-CJZRDCOESA-N (2s)-3-phenyl-2-[[6-[4-[(e)-2-phenylethenyl]phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(\C=C\C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 MVOGOYDQONARRD-CJZRDCOESA-N 0.000 description 2
- WKFYEWXSRFQOKX-UHFFFAOYSA-N 1,4-dioxane;toluene Chemical compound C1COCCO1.CC1=CC=CC=C1 WKFYEWXSRFQOKX-UHFFFAOYSA-N 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 2
- KXCVRJMSLWDHNJ-UHFFFAOYSA-N 1-(9H-fluoren-1-yl)pyrrolidin-2-one Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)N1C(CCC1)=O KXCVRJMSLWDHNJ-UHFFFAOYSA-N 0.000 description 2
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 2
- GQCHXBKCHUWUIB-UHFFFAOYSA-N 1-bromo-4-(3-phenylpropyl)benzene Chemical compound C1=CC(Br)=CC=C1CCCC1=CC=CC=C1 GQCHXBKCHUWUIB-UHFFFAOYSA-N 0.000 description 2
- PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical compound O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 2
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 2
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- XQSJHQXYQAUDFC-UHFFFAOYSA-N 4,6-dichloropyrimidine-5-carbaldehyde Chemical compound ClC1=NC=NC(Cl)=C1C=O XQSJHQXYQAUDFC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- LXKTVNFZAFTUNZ-UHFFFAOYSA-N 5-bromo-2-phenylmethoxypyridine Chemical compound N1=CC(Br)=CC=C1OCC1=CC=CC=C1 LXKTVNFZAFTUNZ-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102100026476 Prostacyclin receptor Human genes 0.000 description 2
- 102000001253 Protein Kinase Human genes 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 102000014384 Type C Phospholipases Human genes 0.000 description 2
- 108010079194 Type C Phospholipases Proteins 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- DAUSGSRIYCUJDK-UHFFFAOYSA-N [4-(phenylcarbamoyl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C(=O)NC1=CC=CC=C1 DAUSGSRIYCUJDK-UHFFFAOYSA-N 0.000 description 2
- 108060000200 adenylate cyclase Proteins 0.000 description 2
- 102000030621 adenylate cyclase Human genes 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- RFSQUDVDHGZTBB-UHFFFAOYSA-N benzyl n-(3-phenylpropyl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NCCCC1=CC=CC=C1 RFSQUDVDHGZTBB-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 235000010216 calcium carbonate Nutrition 0.000 description 2
- 244000309466 calf Species 0.000 description 2
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 210000000265 leukocyte Anatomy 0.000 description 2
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 2
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- ZIVCVDREWVMZRQ-SNVBAGLBSA-N methyl (2r)-2-[(6-chloropyrimidin-4-yl)amino]-3-pyridin-2-ylpropanoate Chemical compound C([C@H](C(=O)OC)NC=1N=CN=C(Cl)C=1)C1=CC=CC=N1 ZIVCVDREWVMZRQ-SNVBAGLBSA-N 0.000 description 2
- KMYAOOYJKZWLRU-LJAQVGFWSA-N methyl (2s)-2-[3-[4-[(3-methoxyphenyl)methoxy]phenyl]anilino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1C=C(C=CC=1)C=1C=CC(OCC=2C=C(OC)C=CC=2)=CC=1)C1=CC=CC=C1 KMYAOOYJKZWLRU-LJAQVGFWSA-N 0.000 description 2
- ISRVJOXERZELHM-VWLOTQADSA-N methyl (2s)-2-[[6-[4-(phenoxymethyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(COC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 ISRVJOXERZELHM-VWLOTQADSA-N 0.000 description 2
- MCOAIMRQYHAVHB-QSAPEBAKSA-N methyl (2s)-2-[[6-[4-[hydroxy(phenyl)methyl]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(=CC=1)C(O)C=1C=CC=CC=1)C1=CC=CC=C1 MCOAIMRQYHAVHB-QSAPEBAKSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- DSWNRHCOGVRDOE-UHFFFAOYSA-N n,n-dimethylmethanimidamide Chemical compound CN(C)C=N DSWNRHCOGVRDOE-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BXPNTXBBAVYAMD-UHFFFAOYSA-N phenyl 2-aminoacetate Chemical compound NCC(=O)OC1=CC=CC=C1 BXPNTXBBAVYAMD-UHFFFAOYSA-N 0.000 description 2
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 235000003270 potassium fluoride Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003174 prostaglandin I2 derivatives Chemical class 0.000 description 2
- 230000002997 prostaglandinlike Effects 0.000 description 2
- 108060006633 protein kinase Proteins 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 230000036303 septic shock Effects 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
- 235000019345 sodium thiosulphate Nutrition 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 239000008223 sterile water Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- MUYLRPZBVHXWPY-UHFFFAOYSA-N tributyl-(6-phenylmethoxypyridin-3-yl)stannane Chemical compound N1=CC([Sn](CCCC)(CCCC)CCCC)=CC=C1OCC1=CC=CC=C1 MUYLRPZBVHXWPY-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 230000024883 vasodilation Effects 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ZAIZDXVMSSDZFA-UHFFFAOYSA-N (1-carboxy-2-phenylethyl)azanium;chloride Chemical compound Cl.OC(=O)C(N)CC1=CC=CC=C1 ZAIZDXVMSSDZFA-UHFFFAOYSA-N 0.000 description 1
- CIGOTTVKYFEEHE-DEOSSOPVSA-N (2S)-2-[[6-[4-(benzylamino)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(NCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 CIGOTTVKYFEEHE-DEOSSOPVSA-N 0.000 description 1
- WNLWFWLTRCLQGD-QRPNPIFTSA-N (2S)-2-amino-3-phenylpropanoic acid methyl acetate Chemical compound C(C)(=O)OC.N[C@@H](CC1=CC=CC=C1)C(=O)O WNLWFWLTRCLQGD-QRPNPIFTSA-N 0.000 description 1
- NKYAUAPTBSOUDC-HSZRJFAPSA-N (2r)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 NKYAUAPTBSOUDC-HSZRJFAPSA-N 0.000 description 1
- ZAIZDXVMSSDZFA-DDWIOCJRSA-N (2r)-2-amino-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.OC(=O)[C@H](N)CC1=CC=CC=C1 ZAIZDXVMSSDZFA-DDWIOCJRSA-N 0.000 description 1
- SKHWPYWUKOPMKE-AWEZNQCLSA-N (2s)-2-(3-bromoanilino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C=C(Br)C=CC=1)C1=CC=CC=C1 SKHWPYWUKOPMKE-AWEZNQCLSA-N 0.000 description 1
- RLIHXKPTGKETCC-QMMMGPOBSA-N (2s)-2-(benzylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NCC1=CC=CC=C1 RLIHXKPTGKETCC-QMMMGPOBSA-N 0.000 description 1
- QYXBNPBZWXNBGN-DFWYDOINSA-N (2s)-2-(methylamino)propanoic acid;hydrochloride Chemical compound Cl.CN[C@@H](C)C(O)=O QYXBNPBZWXNBGN-DFWYDOINSA-N 0.000 description 1
- HNRDSPJCLHNPCR-NDEPHWFRSA-N (2s)-2-[3-[4-[(3-methoxyphenyl)methoxy]phenyl]anilino]-3-phenylpropanoic acid Chemical compound COC1=CC=CC(COC=2C=CC(=CC=2)C=2C=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=CC=2)=C1 HNRDSPJCLHNPCR-NDEPHWFRSA-N 0.000 description 1
- NKYAUAPTBSOUDC-QHCPKHFHSA-N (2s)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=N1 NKYAUAPTBSOUDC-QHCPKHFHSA-N 0.000 description 1
- ZICORNPLGVZWKU-DEOSSOPVSA-N (2s)-2-[[6-[4-(4-methoxyphenyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)C=C1 ZICORNPLGVZWKU-DEOSSOPVSA-N 0.000 description 1
- WVDLOFPQJMHMEE-JIDHJSLPSA-N (2s)-2-[[6-[4-(benzylamino)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid;hydrochloride Chemical compound Cl.C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(NCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WVDLOFPQJMHMEE-JIDHJSLPSA-N 0.000 description 1
- DOSOWINAIXZXBP-NRFANRHFSA-N (2s)-2-[[6-[4-(cyclopropylmethoxy)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC2CC2)=CC=1)C1=CC=CC=C1 DOSOWINAIXZXBP-NRFANRHFSA-N 0.000 description 1
- ULCIHCFGKVIIQR-SFHVURJKSA-N (2s)-2-[[6-[4-(hydroxymethyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C1=CC(CO)=CC=C1C1=CC(N[C@@H](CC=2C=CC=CC=2)C(O)=O)=NC=N1 ULCIHCFGKVIIQR-SFHVURJKSA-N 0.000 description 1
- WCIVSDPGCGNDDJ-DEOSSOPVSA-N (2s)-2-[[6-[4-(phenoxymethyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(COC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WCIVSDPGCGNDDJ-DEOSSOPVSA-N 0.000 description 1
- YCDNYEBBPDRCPP-QHCPKHFHSA-N (2s)-2-[[6-[4-[(3,5-difluorophenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-pyridin-2-ylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=C(F)C=C(F)C=2)=CC=1)C1=CC=CC=N1 YCDNYEBBPDRCPP-QHCPKHFHSA-N 0.000 description 1
- HBRFANHFQXCKEY-SANMLTNESA-N (2s)-2-[[6-[4-[(3,5-dimethoxyphenyl)methoxy]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound COC1=CC(OC)=CC(COC=2C=CC(=CC=2)C=2N=CN=C(N[C@@H](CC=3C=CC=CC=3)C(O)=O)C=2)=C1 HBRFANHFQXCKEY-SANMLTNESA-N 0.000 description 1
- NDGKZGJBYJLMNO-ZCGOLBPFSA-N (2s)-2-[[6-[4-[(e)-phenoxyiminomethyl]phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(\C=N\OC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 NDGKZGJBYJLMNO-ZCGOLBPFSA-N 0.000 description 1
- UHYBQLHLHAROJR-QMMMGPOBSA-N (2s)-2-amino-3-phenylpropanehydrazide Chemical compound NNC(=O)[C@@H](N)CC1=CC=CC=C1 UHYBQLHLHAROJR-QMMMGPOBSA-N 0.000 description 1
- WPIWAEAPTLYFQX-DEOSSOPVSA-N (2s)-3-(3-hydroxyphenyl)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC(O)=C1 WPIWAEAPTLYFQX-DEOSSOPVSA-N 0.000 description 1
- DIJXGISWAISVKY-SANMLTNESA-N (2s)-3-[3-(2-aminoethoxy)phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound NCCOC1=CC=CC(C[C@H](NC=2N=CN=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(O)=O)=C1 DIJXGISWAISVKY-SANMLTNESA-N 0.000 description 1
- VHRQEXNVXIPCBD-SANMLTNESA-N (2s)-3-[4-(4,5-dihydro-1h-imidazol-2-ylamino)phenyl]-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C(C=C1)=CC=C1NC1=NCCN1 VHRQEXNVXIPCBD-SANMLTNESA-N 0.000 description 1
- RRONHWAVOYADJL-HNNXBMFYSA-N (2s)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 RRONHWAVOYADJL-HNNXBMFYSA-N 0.000 description 1
- KAHVGXJMZRSISH-MHZLTWQESA-N (2s)-3-phenyl-2-[3-(4-phenylmethoxyphenyl)anilino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1C=C(C=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 KAHVGXJMZRSISH-MHZLTWQESA-N 0.000 description 1
- WVMAVBNJFVOZSE-DEOSSOPVSA-N (2s)-3-phenyl-2-[[4-(4-phenylmethoxyphenyl)pyrimidin-2-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=C(C=CN=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WVMAVBNJFVOZSE-DEOSSOPVSA-N 0.000 description 1
- LJWRRKQTPFBURL-QFIPXVFZSA-N (2s)-3-phenyl-2-[[6-(6-phenylmethoxypyridin-3-yl)pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=NC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 LJWRRKQTPFBURL-QFIPXVFZSA-N 0.000 description 1
- HUSLMJUCDVNJDH-VWLOTQADSA-N (2s)-3-phenyl-2-[[6-[4-(2-phenylethyl)phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(CCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 HUSLMJUCDVNJDH-VWLOTQADSA-N 0.000 description 1
- MVOGOYDQONARRD-MQCQLYSJSA-N (2s)-3-phenyl-2-[[6-[4-[(z)-2-phenylethenyl]phenyl]pyrimidin-4-yl]amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC=1N=CN=C(C=1)C=1C=CC(\C=C/C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 MVOGOYDQONARRD-MQCQLYSJSA-N 0.000 description 1
- PHVSUUGFGMGZPE-UHFFFAOYSA-N (4-bromophenyl)carbamic acid Chemical compound OC(=O)NC1=CC=C(Br)C=C1 PHVSUUGFGMGZPE-UHFFFAOYSA-N 0.000 description 1
- BKDJQJVIUNBERD-UHFFFAOYSA-N (4-phenylmethoxyphenoxy)boronic acid Chemical compound C1=CC(OB(O)O)=CC=C1OCC1=CC=CC=C1 BKDJQJVIUNBERD-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical class 0.000 description 1
- JEJGXSYTABEOKP-UHFFFAOYSA-N (benzylamino)carbamic acid Chemical compound OC(=O)NNCC1=CC=CC=C1 JEJGXSYTABEOKP-UHFFFAOYSA-N 0.000 description 1
- LLCKXLBGFBTDHO-UPHRSURJSA-N (z)-2,3-difluoroprop-2-enoic acid Chemical compound OC(=O)C(\F)=C\F LLCKXLBGFBTDHO-UPHRSURJSA-N 0.000 description 1
- ZOWSTJBTHYZCNM-UHFFFAOYSA-N 1,2,2,3,3,4-hexamethyl-4H-pyridine Chemical compound CC1C(C(N(C=C1)C)(C)C)(C)C ZOWSTJBTHYZCNM-UHFFFAOYSA-N 0.000 description 1
- WOAHJDHKFWSLKE-UHFFFAOYSA-N 1,2-benzoquinone Chemical compound O=C1C=CC=CC1=O WOAHJDHKFWSLKE-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- INQSMEFCAIHTJG-UHFFFAOYSA-N 1,3-dimethyl-7h-purine-2,6-dione;hydrate Chemical group O.O=C1N(C)C(=O)N(C)C2=C1NC=N2 INQSMEFCAIHTJG-UHFFFAOYSA-N 0.000 description 1
- WORJRXHJTUTINR-UHFFFAOYSA-N 1,4-dioxane;hydron;chloride Chemical compound Cl.C1COCCO1 WORJRXHJTUTINR-UHFFFAOYSA-N 0.000 description 1
- MKYMYZJJFMPDOA-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 MKYMYZJJFMPDOA-UHFFFAOYSA-N 0.000 description 1
- ZKSOJQDNSNJIQW-UHFFFAOYSA-N 1-(bromomethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CBr)=C1 ZKSOJQDNSNJIQW-UHFFFAOYSA-N 0.000 description 1
- DWCTVGYGXSIFST-UHFFFAOYSA-N 1-(cyclopropylmethoxy)-4-iodobenzene Chemical compound C1=CC(I)=CC=C1OCC1CC1 DWCTVGYGXSIFST-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- ATWYGJDEMZGTHV-UHFFFAOYSA-N 2,3-diamino-4-phenylbutanoic acid Chemical compound OC(=O)C(N)C(N)CC1=CC=CC=C1 ATWYGJDEMZGTHV-UHFFFAOYSA-N 0.000 description 1
- BTTNYQZNBZNDOR-UHFFFAOYSA-N 2,4-dichloropyrimidine Chemical compound ClC1=CC=NC(Cl)=N1 BTTNYQZNBZNDOR-UHFFFAOYSA-N 0.000 description 1
- ZHXUWDPHUQHFOV-UHFFFAOYSA-N 2,5-dibromopyridine Chemical compound BrC1=CC=C(Br)N=C1 ZHXUWDPHUQHFOV-UHFFFAOYSA-N 0.000 description 1
- GQPIEFFYGONFTJ-UHFFFAOYSA-N 2-(3-morpholin-4-ylpropyl)benzo[de]isoquinoline-1,3-dione Chemical compound O=C1C(C=23)=CC=CC3=CC=CC=2C(=O)N1CCCN1CCOCC1 GQPIEFFYGONFTJ-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- UTIMBUCRNZURQB-UHFFFAOYSA-N 2-(propylamino)propanoic acid Chemical compound CCCNC(C)C(O)=O UTIMBUCRNZURQB-UHFFFAOYSA-N 0.000 description 1
- PPKAIMDMNWBOKN-UHFFFAOYSA-N 2-Oxo-4-phenylbutyric acid Chemical compound OC(=O)C(=O)CCC1=CC=CC=C1 PPKAIMDMNWBOKN-UHFFFAOYSA-N 0.000 description 1
- SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
- WWSJZGAPAVMETJ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethoxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OCC WWSJZGAPAVMETJ-UHFFFAOYSA-N 0.000 description 1
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- QRXBTPFMCTXCRD-UHFFFAOYSA-N 2-chloropyridine-4-carbonitrile Chemical compound ClC1=CC(C#N)=CC=N1 QRXBTPFMCTXCRD-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- ILJKKAIQFPEIBL-UHFFFAOYSA-N 2-cyclopropyl-2-hydroxyacetonitrile Chemical compound N#CC(O)C1CC1 ILJKKAIQFPEIBL-UHFFFAOYSA-N 0.000 description 1
- SGLADJJYQDGSEJ-UHFFFAOYSA-N 2-ethyl-n,n-dimethylaniline Chemical compound CCC1=CC=CC=C1N(C)C SGLADJJYQDGSEJ-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- NDAJNMAAXXIADY-UHFFFAOYSA-N 2-methylpropanimidamide Chemical compound CC(C)C(N)=N NDAJNMAAXXIADY-UHFFFAOYSA-N 0.000 description 1
- SGDSYOQTEPOINS-UHFFFAOYSA-N 2-methylsulfanyl-4-(4-phenylmethoxyphenyl)pyrimidine Chemical compound CSC1=NC=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 SGDSYOQTEPOINS-UHFFFAOYSA-N 0.000 description 1
- WEOKJKNWWAYGQN-UHFFFAOYSA-N 2-methylsulfonyl-4-(4-phenylmethoxyphenyl)pyrimidine Chemical compound CS(=O)(=O)C1=NC=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 WEOKJKNWWAYGQN-UHFFFAOYSA-N 0.000 description 1
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 description 1
- DHYHYLGCQVVLOQ-UHFFFAOYSA-N 3-bromoaniline Chemical compound NC1=CC=CC(Br)=C1 DHYHYLGCQVVLOQ-UHFFFAOYSA-N 0.000 description 1
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
- 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ACGOYQVBNIIMJN-UHFFFAOYSA-N 4,6-diaminopyrimidine-5-carbaldehyde Chemical compound NC1=NC=NC(N)=C1C=O ACGOYQVBNIIMJN-UHFFFAOYSA-N 0.000 description 1
- LBVUFZJYMWUZIW-UHFFFAOYSA-N 4,6-diiodopyrimidine Chemical compound IC1=CC(I)=NC=N1 LBVUFZJYMWUZIW-UHFFFAOYSA-N 0.000 description 1
- BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- ZRYZBQLXDKPBDU-UHFFFAOYSA-N 4-bromobenzaldehyde Chemical compound BrC1=CC=C(C=O)C=C1 ZRYZBQLXDKPBDU-UHFFFAOYSA-N 0.000 description 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- TWSIYGATPWEKBK-UHFFFAOYSA-N 4h-1,3-benzodioxine Chemical compound C1=CC=C2OCOCC2=C1 TWSIYGATPWEKBK-UHFFFAOYSA-N 0.000 description 1
- IDFUCAQPSWKWKX-UHFFFAOYSA-N 6-(4-phenylmethoxyphenyl)-n-[2-phenyl-1-(2h-tetrazol-5-yl)ethyl]pyrimidin-4-amine Chemical compound C=1C=CC=CC=1COC(C=C1)=CC=C1C(N=CN=1)=CC=1NC(C=1NN=NN=1)CC1=CC=CC=C1 IDFUCAQPSWKWKX-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- VVCRRRYJVLKZKM-UHFFFAOYSA-N 6-iodo-n-[2-phenyl-1-[1-(2-trimethylsilylethoxymethyl)tetrazol-5-yl]ethyl]pyrimidin-4-amine Chemical compound C[Si](C)(C)CCOCN1N=NN=C1C(NC=1N=CN=C(I)C=1)CC1=CC=CC=C1 VVCRRRYJVLKZKM-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- XDFXGWOHYFKJLH-UHFFFAOYSA-N C(=O)(O)C1=CC=C(C=C1)COB(O)O Chemical compound C(=O)(O)C1=CC=C(C=C1)COB(O)O XDFXGWOHYFKJLH-UHFFFAOYSA-N 0.000 description 1
- XYYMQCOGWFQSEQ-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)N(C(C)=N)C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)N(C(C)=N)C1=CC=CC=2C3=CC=CC=C3CC12 XYYMQCOGWFQSEQ-UHFFFAOYSA-N 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 238000009641 CAMP test Methods 0.000 description 1
- RTFOHTBMUZVSQZ-UHFFFAOYSA-N CCCNN(NCC)C(C)(C)NC Chemical compound CCCNN(NCC)C(C)(C)NC RTFOHTBMUZVSQZ-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- ZVLJZRYKZGEDGT-NDEPHWFRSA-N CN(C1=CC=CC(=C1)C2=CC=C(C=C2)OCC3=CC=CC=C3)[C@@H](CC4=CC=CC=C4)C(=O)O Chemical compound CN(C1=CC=CC(=C1)C2=CC=C(C=C2)OCC3=CC=CC=C3)[C@@H](CC4=CC=CC=C4)C(=O)O ZVLJZRYKZGEDGT-NDEPHWFRSA-N 0.000 description 1
- IPGCGOUHJHBDLG-VWLOTQADSA-N CN(C1=NC=NC(=C1)C2=CC=C(C=C2)CC3=CC=CC=C3)[C@@H](CC4=CC=CC=C4)C(=O)O Chemical compound CN(C1=NC=NC(=C1)C2=CC=C(C=C2)CC3=CC=CC=C3)[C@@H](CC4=CC=CC=C4)C(=O)O IPGCGOUHJHBDLG-VWLOTQADSA-N 0.000 description 1
- WGMCZHRFHGPKJS-SFHVURJKSA-N CN(C1=NC=NC(=C1)C2=CC=C(C=C2)O)[C@@H](CC3=CC=CC=C3)C(=O)O Chemical compound CN(C1=NC=NC(=C1)C2=CC=C(C=C2)O)[C@@H](CC3=CC=CC=C3)C(=O)O WGMCZHRFHGPKJS-SFHVURJKSA-N 0.000 description 1
- VWDLKLLFDCKDDH-SANMLTNESA-N CN([C@@H](CC1=CC=CC=C1)C(=O)O)C1=NC=NC(=C1)C1=CC=C(C=C1)C#CC1=CC=CC=C1 Chemical compound CN([C@@H](CC1=CC=CC=C1)C(=O)O)C1=NC=NC(=C1)C1=CC=C(C=C1)C#CC1=CC=CC=C1 VWDLKLLFDCKDDH-SANMLTNESA-N 0.000 description 1
- GNXBVHORNNHYJT-LJAQVGFWSA-N CN([C@@H](CC1=CC=CC=C1)C(=O)O)C=1C=C(C=CC1)C1=CC=C(C=C1)OCC1=CC(=CC=C1)OC Chemical compound CN([C@@H](CC1=CC=CC=C1)C(=O)O)C=1C=C(C=CC1)C1=CC=C(C=C1)OCC1=CC(=CC=C1)OC GNXBVHORNNHYJT-LJAQVGFWSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 241000272165 Charadriidae Species 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 102000008130 Cyclic AMP-Dependent Protein Kinases Human genes 0.000 description 1
- 108010049894 Cyclic AMP-Dependent Protein Kinases Proteins 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LRQKBLKVPFOOQJ-RXMQYKEDSA-N D-norleucine Chemical compound CCCC[C@@H](N)C(O)=O LRQKBLKVPFOOQJ-RXMQYKEDSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 238000008157 ELISA kit Methods 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- IKYCZSUNGFRBJS-UHFFFAOYSA-N Euphorbia factor RL9 = U(1) = Resiniferatoxin Natural products COC1=CC(O)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 IKYCZSUNGFRBJS-UHFFFAOYSA-N 0.000 description 1
- MKAAPRRCXZSUET-UHFFFAOYSA-N FC1=C(C(=C(C=2CC3=CC=CC=C3C12)S(=O)(=O)OS(=O)(=O)C1=C(C(=C(C=2C3=CC=CC=C3CC12)F)F)F)F)F Chemical compound FC1=C(C(=C(C=2CC3=CC=CC=C3C12)S(=O)(=O)OS(=O)(=O)C1=C(C(=C(C=2C3=CC=CC=C3CC12)F)F)F)F)F MKAAPRRCXZSUET-UHFFFAOYSA-N 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- FWCXELAAYFYCSR-RYKNUXCGSA-N Gitogenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O)C[C@@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 FWCXELAAYFYCSR-RYKNUXCGSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000012981 Hank's balanced salt solution Substances 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 206010021639 Incontinence Diseases 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100189356 Mus musculus Papolb gene Proteins 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- PMTGXDAKINWIEX-UHFFFAOYSA-N N.N.N.N Chemical compound N.N.N.N PMTGXDAKINWIEX-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 102100040460 P2X purinoceptor 3 Human genes 0.000 description 1
- 101710189970 P2X purinoceptor 3 Proteins 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 101710170814 Prostacyclin receptor Proteins 0.000 description 1
- 101100067573 Pseudomonas putida (strain ATCC 47054 / DSM 6125 / CFBP 8728 / NCIMB 11950 / KT2440) pgi2 gene Proteins 0.000 description 1
- 239000012980 RPMI-1640 medium Substances 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- APJYDQYYACXCRM-UHFFFAOYSA-N Tryptamine Natural products C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- SGDCDCNVOIOFNU-UHFFFAOYSA-N [4-(3-phenylpropyl)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1CCCC1=CC=CC=C1 SGDCDCNVOIOFNU-UHFFFAOYSA-N 0.000 description 1
- AYJVDOMUBHORKK-UHFFFAOYSA-N [4-(cyclopropylmethoxy)phenyl]boronic acid Chemical compound C1=CC(B(O)O)=CC=C1OCC1CC1 AYJVDOMUBHORKK-UHFFFAOYSA-N 0.000 description 1
- JHZICVAIDBTSOQ-UHFFFAOYSA-N [O-2].[Na+].[Ar].[Na+] Chemical compound [O-2].[Na+].[Ar].[Na+] JHZICVAIDBTSOQ-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- IRTLGLYSFAKASM-UHFFFAOYSA-N acetic acid;propan-2-ol Chemical compound CC(C)O.CC(O)=O IRTLGLYSFAKASM-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 210000003766 afferent neuron Anatomy 0.000 description 1
- 230000004520 agglutination Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005277 alkyl imino group Chemical group 0.000 description 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 208000028004 allergic respiratory disease Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000006242 amine protecting group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- VWZPEJBSKVAQHV-UHFFFAOYSA-N argon;triphenylphosphane Chemical compound [Ar].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VWZPEJBSKVAQHV-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- ZRBROGSAUIUIJE-UHFFFAOYSA-N azanium;azane;chloride Chemical compound N.[NH4+].[Cl-] ZRBROGSAUIUIJE-UHFFFAOYSA-N 0.000 description 1
- 125000002785 azepinyl group Chemical group 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 229940092782 bentonite Drugs 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- OYNUPIUEKUPWOE-UHFFFAOYSA-N benzyl n-(1-cyano-2-phenylethyl)carbamate Chemical compound C=1C=CC=CC=1COC(=O)NC(C#N)CC1=CC=CC=C1 OYNUPIUEKUPWOE-UHFFFAOYSA-N 0.000 description 1
- LHKKUYDIFGSCGS-UHFFFAOYSA-N benzyl sulfamate Chemical compound NS(=O)(=O)OCC1=CC=CC=C1 LHKKUYDIFGSCGS-UHFFFAOYSA-N 0.000 description 1
- SVEKJHBWJWHXKV-UHFFFAOYSA-N benzylsulfamic acid Chemical compound OS(=O)(=O)NCC1=CC=CC=C1 SVEKJHBWJWHXKV-UHFFFAOYSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 238000009534 blood test Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- 125000005382 boronyl group Chemical group 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 235000011116 calcium hydroxide Nutrition 0.000 description 1
- 235000017663 capsaicin Nutrition 0.000 description 1
- 229960002504 capsaicin Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- VNWKTOKETHGBQD-YPZZEJLDSA-N carbane Chemical class [10CH4] VNWKTOKETHGBQD-YPZZEJLDSA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 210000001627 cerebral artery Anatomy 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125890 compound Ia Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- MVHPKFQBHWGTQH-UHFFFAOYSA-N cyano(nitro)carbamic acid Chemical compound OC(=O)N(C#N)[N+]([O-])=O MVHPKFQBHWGTQH-UHFFFAOYSA-N 0.000 description 1
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 210000004268 dentin Anatomy 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- XLQDQRMFMXYSQS-UHFFFAOYSA-N dichloromethane;hydrochloride Chemical compound Cl.ClCCl XLQDQRMFMXYSQS-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000002224 dissection Methods 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- AWRWFICXGYUPDI-SANMLTNESA-N ethyl (2s)-3-(3-hydroxyphenyl)-2-[[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OCC)NC=1N=CN=C(C=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC(O)=C1 AWRWFICXGYUPDI-SANMLTNESA-N 0.000 description 1
- FDEGVCFFEKCZBP-NDEPHWFRSA-N ethyl (2s)-3-phenyl-2-[[2-(4-phenylmethoxyphenyl)pyridin-4-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OCC)NC=1C=C(N=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 FDEGVCFFEKCZBP-NDEPHWFRSA-N 0.000 description 1
- CJTQEHIQEPBAAT-UHFFFAOYSA-N ethyl 2-(3-hydroxyphenyl)propanoate Chemical compound CCOC(=O)C(C)C1=CC=CC(O)=C1 CJTQEHIQEPBAAT-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- ZETBYFYOBYYVOE-UHFFFAOYSA-N ethyl n-(4-bromophenyl)carbamate Chemical compound CCOC(=O)NC1=CC=C(Br)C=C1 ZETBYFYOBYYVOE-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 150000002220 fluorenes Chemical class 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 230000003862 health status Effects 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000004047 hyperresponsiveness Effects 0.000 description 1
- HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 description 1
- 229960002240 iloprost Drugs 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229910000462 iron(III) oxide hydroxide Inorganic materials 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VSDUZFOSJDMAFZ-SECBINFHSA-N methyl (2r)-2-amino-3-phenylpropanoate Chemical compound COC(=O)[C@H](N)CC1=CC=CC=C1 VSDUZFOSJDMAFZ-SECBINFHSA-N 0.000 description 1
- NTGMUWGHRHMBMO-NSHDSACASA-N methyl (2s)-2-[(2-chloropyrimidin-4-yl)amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=C(Cl)N=CC=1)C1=CC=CC=C1 NTGMUWGHRHMBMO-NSHDSACASA-N 0.000 description 1
- GFJPYXPAOILVMM-NRFANRHFSA-N methyl (2s)-2-[3-(4-hydroxyphenyl)anilino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1C=C(C=CC=1)C=1C=CC(O)=CC=1)C1=CC=CC=C1 GFJPYXPAOILVMM-NRFANRHFSA-N 0.000 description 1
- QEOXTWYBNVNVMJ-FERBBOLQSA-N methyl (2s)-2-[[6-(4-aminophenyl)pyrimidin-4-yl]amino]-3-phenylpropanoate;hydrochloride Chemical compound Cl.C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(N)=CC=1)C1=CC=CC=C1 QEOXTWYBNVNVMJ-FERBBOLQSA-N 0.000 description 1
- HKYUFZUYPHRRNA-VWLOTQADSA-N methyl (2s)-2-[[6-(4-benzylphenyl)pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(CC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 HKYUFZUYPHRRNA-VWLOTQADSA-N 0.000 description 1
- FPWHPHSWLBOJER-QHCPKHFHSA-N methyl (2s)-2-[[6-[4-(4-cyanopyridin-2-yl)oxyphenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(OC=2N=CC=C(C=2)C#N)=CC=1)C1=CC=CC=C1 FPWHPHSWLBOJER-QHCPKHFHSA-N 0.000 description 1
- XIZCJUNHWMIMPE-VWLOTQADSA-N methyl (2s)-2-[[6-[4-(4-methoxyphenyl)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(=CC=1)C=1C=CC(OC)=CC=1)C1=CC=CC=C1 XIZCJUNHWMIMPE-VWLOTQADSA-N 0.000 description 1
- GPXBRGKMXJZARG-QFIPXVFZSA-N methyl (2s)-2-[[6-[4-(cyclopropylmethylamino)phenyl]pyrimidin-4-yl]amino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(NCC2CC2)=CC=1)C1=CC=CC=C1 GPXBRGKMXJZARG-QFIPXVFZSA-N 0.000 description 1
- PYWIBQCIUNGTJX-NDEPHWFRSA-N methyl (2s)-3-phenyl-2-[3-(4-phenylmethoxyphenyl)anilino]propanoate Chemical compound C([C@@H](C(=O)OC)NC=1C=C(C=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 PYWIBQCIUNGTJX-NDEPHWFRSA-N 0.000 description 1
- WFAQXJWZXRFKAZ-DEOSSOPVSA-N methyl (2s)-3-phenyl-2-[[2-(4-phenylmethoxyphenyl)pyrimidin-4-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=C(N=CC=1)C=1C=CC(OCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 WFAQXJWZXRFKAZ-DEOSSOPVSA-N 0.000 description 1
- QHWFXUXAJSXRCW-SANMLTNESA-N methyl (2s)-3-phenyl-2-[[6-[4-(2-phenylethyl)phenyl]pyrimidin-4-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(CCC=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 QHWFXUXAJSXRCW-SANMLTNESA-N 0.000 description 1
- MTNOABJZYNLAQW-JYSHFMIGSA-N methyl (2s)-3-phenyl-2-[[6-[4-[(e)-2-phenylethenyl]phenyl]pyrimidin-4-yl]amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC=1N=CN=C(C=1)C=1C=CC(\C=C\C=2C=CC=CC=2)=CC=1)C1=CC=CC=C1 MTNOABJZYNLAQW-JYSHFMIGSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- IZXGZAJMDLJLMF-UHFFFAOYSA-N methylaminomethanol Chemical compound CNCO IZXGZAJMDLJLMF-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- FEKRFYZGYUTGRY-UHFFFAOYSA-N n'-ethylmethanediimine Chemical compound CCN=C=N FEKRFYZGYUTGRY-UHFFFAOYSA-N 0.000 description 1
- CPAOZIMTJFGGRP-UHFFFAOYSA-N n,n-bis(9h-fluoren-1-yl)-9h-fluoren-1-amine Chemical compound C1C2=CC=CC=C2C2=C1C(N(C=1C3=C(C4=CC=CC=C4C3)C=CC=1)C=1C=CC=C3C4=CC=CC=C4CC=13)=CC=C2 CPAOZIMTJFGGRP-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
- FTEKLZONWYPLCZ-UHFFFAOYSA-N n-(3-phenylpropyl)hydroxylamine Chemical compound ONCCCC1=CC=CC=C1 FTEKLZONWYPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- SCIFESDRCALIIM-UHFFFAOYSA-N n-methylphenylalanine Chemical compound CNC(C(O)=O)CC1=CC=CC=C1 SCIFESDRCALIIM-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000003957 neurotransmitter release Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003040 nociceptive effect Effects 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000005447 octyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000008058 pain sensation Effects 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- YBVNFKZSMZGRAD-UHFFFAOYSA-N pentamidine isethionate Chemical compound OCCS(O)(=O)=O.OCCS(O)(=O)=O.C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 YBVNFKZSMZGRAD-UHFFFAOYSA-N 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- DSDNAKHZNJAGHN-UHFFFAOYSA-N resinferatoxin Natural products C1=C(O)C(OC)=CC(CC(=O)OCC=2CC3(O)C(=O)C(C)=CC3C34C(C)CC5(OC(O4)(CC=4C=CC=CC=4)OC5C3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-UHFFFAOYSA-N 0.000 description 1
- DSDNAKHZNJAGHN-MXTYGGKSSA-N resiniferatoxin Chemical compound C1=C(O)C(OC)=CC(CC(=O)OCC=2C[C@]3(O)C(=O)C(C)=C[C@H]3[C@@]34[C@H](C)C[C@@]5(O[C@@](O4)(CC=4C=CC=CC=4)O[C@@H]5[C@@H]3C=2)C(C)=C)=C1 DSDNAKHZNJAGHN-MXTYGGKSSA-N 0.000 description 1
- 229940073454 resiniferatoxin Drugs 0.000 description 1
- 201000004335 respiratory allergy Diseases 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012465 retentate Substances 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 210000001032 spinal nerve Anatomy 0.000 description 1
- 238000013223 sprague-dawley female rat Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000004354 sulfur functional group Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- QOISWWBTZMFUEL-UHFFFAOYSA-N tert-butyl 2-amino-3-phenylpropanoate Chemical compound CC(C)(C)OC(=O)C(N)CC1=CC=CC=C1 QOISWWBTZMFUEL-UHFFFAOYSA-N 0.000 description 1
- MKEUJYLWUDYPAQ-UHFFFAOYSA-N tert-butyl n-benzyl-n-(4-bromophenyl)carbamate Chemical compound C=1C=C(Br)C=CC=1N(C(=O)OC(C)(C)C)CC1=CC=CC=C1 MKEUJYLWUDYPAQ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IFXORIIYQORRMJ-UHFFFAOYSA-N tribenzylphosphane Chemical compound C=1C=CC=CC=1CP(CC=1C=CC=CC=1)CC1=CC=CC=C1 IFXORIIYQORRMJ-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical group CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000005289 uranyl group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/04—Antihaemorrhagics; Procoagulants; Haemostatic agents; Antifibrinolytic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
-
- 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
- C07C229/34—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 containing six-membered aromatic rings
- C07C229/36—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 containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- 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
- C07D213/60—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Rheumatology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02025024 | 2002-11-11 | ||
| EP03011397 | 2003-05-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200418799A true TW200418799A (en) | 2004-10-01 |
Family
ID=32313830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092131351A TW200418799A (en) | 2002-11-11 | 2003-11-10 | Phenyl or heteroaryl amino alkane derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US20060089371A1 (enExample) |
| EP (1) | EP1575919A1 (enExample) |
| JP (1) | JP2006514110A (enExample) |
| KR (1) | KR20050074571A (enExample) |
| AR (1) | AR042023A1 (enExample) |
| AU (1) | AU2003276201A1 (enExample) |
| BR (1) | BR0316191A (enExample) |
| CA (1) | CA2505361A1 (enExample) |
| CO (1) | CO5580824A2 (enExample) |
| EC (1) | ECSP055789A (enExample) |
| HN (1) | HN2003000353A (enExample) |
| HR (1) | HRP20050529A2 (enExample) |
| MA (1) | MA27491A1 (enExample) |
| NO (1) | NO20052797L (enExample) |
| PE (1) | PE20040672A1 (enExample) |
| PL (1) | PL376993A1 (enExample) |
| TW (1) | TW200418799A (enExample) |
| UY (1) | UY28072A1 (enExample) |
| WO (1) | WO2004043926A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE327744T1 (de) | 2001-03-20 | 2006-06-15 | Sanol Arznei Schwarz Gmbh | Neue verwendung von peptidverbindungen bei der behandlung von nicht-neuropathischem entzündungsschmerz |
| ATE228358T1 (de) | 2001-03-21 | 2002-12-15 | Sanol Arznei Schwarz Gmbh | Neue verwendung einer klasse von peptidverbindungen zur behandlung von allodynie oder andere arten von chronischen oder phantomschmerzen |
| AU2004294714B2 (en) | 2003-12-02 | 2009-12-10 | Ucb Pharma Gmbh | Novel use of peptide compounds for treating central neuropathic pain |
| KR101260717B1 (ko) | 2003-12-03 | 2013-05-09 | 와이엠 바이오사이언시즈 오스트레일리아 피티와이 엘티디 | 튜불린 저해제 |
| EP1604655A1 (en) | 2004-06-09 | 2005-12-14 | Schwarz Pharma Ag | Novel use of peptide compounds for treating pain in trigeminal neuralgia |
| JP2008510758A (ja) | 2004-08-27 | 2008-04-10 | シュヴァルツ・ファーマ・アーゲー | 骨肉腫の痛み、化学療法誘発性及びヌクレオシド誘発性の痛みを治療するためのペプチド化合物の新規使用 |
| WO2006029735A1 (en) * | 2004-09-15 | 2006-03-23 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with prostaglandin 12 receptor (ptgir) |
| HN2005000795A (es) * | 2004-10-15 | 2010-08-19 | Aventis Pharma Inc | Pirimidinas como antagonistas del receptor de prostaglandina d2 |
| PE20070404A1 (es) * | 2005-07-29 | 2007-05-10 | Wyeth Corp | Compuestos derivados de cianopirrol-sulfonamida como moduladores del receptor de progesterona |
| PE20070182A1 (es) | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
| PE20070341A1 (es) * | 2005-07-29 | 2007-04-13 | Wyeth Corp | Derivados de pirrol como moduladores del receptor de progesterona |
| JP2009503103A (ja) | 2005-08-02 | 2009-01-29 | レキシコン・ファーマシューティカルズ・インコーポレーテッド | アリールピリジン及びその使用方法 |
| JP5443981B2 (ja) | 2006-06-15 | 2014-03-19 | ウーツェーベー ファルマ ゲーエムベーハー | 相乗的抗痙攣効果を有する医薬組成物 |
| US20080242694A1 (en) * | 2006-09-18 | 2008-10-02 | D Sidocky Neil R | Amino-substituted heterocycles, compositions thereof, and methods of treatment therewith |
| JO3598B1 (ar) * | 2006-10-10 | 2020-07-05 | Infinity Discovery Inc | الاحماض والاسترات البورونية كمثبطات اميد هيدروليز الحامض الدهني |
| WO2009132310A1 (en) | 2008-04-25 | 2009-10-29 | Wisconsin Alumni Research Foundation | Inhibitors of udp-galactopyranose mutase thwart mycobacterial growth |
| US20100060985A1 (en) | 2008-09-09 | 2010-03-11 | Fujifilm Corporation | Method for producing polarizing plate, and automobile's windshield |
| PE20110843A1 (es) | 2008-09-22 | 2011-12-08 | Cayman Chem Co | Derivados de 5-(1h-imidazol-5-il)-2-fenilpirimidina, como inhibidores de prostaglandina d sintasa hematopoyetica |
| AR081331A1 (es) | 2010-04-23 | 2012-08-08 | Cytokinetics Inc | Amino- pirimidinas composiciones de las mismas y metodos para el uso de los mismos |
| AR081626A1 (es) | 2010-04-23 | 2012-10-10 | Cytokinetics Inc | Compuestos amino-piridazinicos, composiciones farmaceuticas que los contienen y uso de los mismos para tratar trastornos musculares cardiacos y esqueleticos |
| EP2560488B1 (en) | 2010-04-23 | 2015-10-28 | Cytokinetics, Inc. | Certain amino-pyridines and amino-triazines, compositions thereof, and methods for their use |
| US8759380B2 (en) | 2011-04-22 | 2014-06-24 | Cytokinetics, Inc. | Certain heterocycles, compositions thereof, and methods for their use |
| TW201444798A (zh) | 2013-02-28 | 2014-12-01 | 必治妥美雅史谷比公司 | 作爲強效rock1及rock2抑制劑之苯基吡唑衍生物 |
| EP2961746B1 (en) | 2013-02-28 | 2018-01-03 | Bristol-Myers Squibb Company | Phenylpyrazole derivatives as potent rock1 and rock2 inhibitors |
| TR201907981T4 (tr) | 2013-06-27 | 2019-06-21 | Pfizer | Heteroaromatik bileşikler ve bunların dopamin d1 ligandları olarak kullanımı. |
| US9828393B2 (en) * | 2013-07-22 | 2017-11-28 | The Regents Of The University Of Colorado, A Body Corporate | Silylalkyloxyaryl compounds and methods for treating cancer |
| US9994547B2 (en) | 2014-10-06 | 2018-06-12 | Takeda Pharmaceutical Company Limited | Heteroarylamide inhibitors of TBK1 |
| US10080757B2 (en) | 2016-03-11 | 2018-09-25 | Wisconsin Alumni Research Foundation | Inhibitors of UDP-galactopyranose mutase |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4259489A (en) * | 1977-12-22 | 1981-03-31 | Kyowa Gas Chemical Industry Co. Ltd. | 2,3-Dicyanopyrazines |
| WO1996033972A1 (en) * | 1995-04-28 | 1996-10-31 | Glaxo Group Limited | Methods for synthesizing diverse collections of pyridines, pyrimidines, 1,4-dihydro derivatives thereof, and piperidine derivatives |
| IL129820A0 (en) * | 1996-12-23 | 2000-02-29 | Elan Pharm Inc | Cycloalkyl lactam lactone and related compounds as beta-amyloid peptide release inhibitors |
| GB2323842A (en) * | 1997-04-04 | 1998-10-07 | Ferring Bv | Pyridine derivatives |
| AU2623900A (en) * | 1999-01-22 | 2000-08-07 | American Home Products Corporation | Compounds which inhibit leukocyte adhesion mediated by vla-4 |
| US20020058606A1 (en) * | 1999-05-10 | 2002-05-16 | Gonzalez Maria Isabel | Treatment of sexual dysfunction |
| HRP20020733A2 (en) * | 2000-03-16 | 2005-02-28 | F. Hoffmann - La Roche Ag | Carboxylic acid derivatives as ip antagonists |
| AU2002223802A1 (en) * | 2000-11-17 | 2002-05-27 | Warner-Lambert Company Llc | Treatment of sexual dysfunction with non peptide bombesin receptor antagonists |
| US6933290B2 (en) * | 2001-05-30 | 2005-08-23 | Novartis Ag | 2-{N-(2-amino-3-(heteroaryl or aryl)propionyl)-aminoacyl}-amino}-alkylboronic acid derivatives |
-
2003
- 2003-10-29 EP EP03810952A patent/EP1575919A1/en not_active Withdrawn
- 2003-10-29 HR HR20050529A patent/HRP20050529A2/xx not_active Application Discontinuation
- 2003-10-29 US US10/534,174 patent/US20060089371A1/en not_active Abandoned
- 2003-10-29 BR BR0316191-9A patent/BR0316191A/pt not_active IP Right Cessation
- 2003-10-29 PL PL376993A patent/PL376993A1/pl unknown
- 2003-10-29 JP JP2005506646A patent/JP2006514110A/ja active Pending
- 2003-10-29 CA CA002505361A patent/CA2505361A1/en not_active Abandoned
- 2003-10-29 AU AU2003276201A patent/AU2003276201A1/en not_active Abandoned
- 2003-10-29 KR KR1020057008288A patent/KR20050074571A/ko not_active Withdrawn
- 2003-10-29 WO PCT/EP2003/011976 patent/WO2004043926A1/en not_active Ceased
- 2003-11-07 UY UY28072A patent/UY28072A1/es not_active Application Discontinuation
- 2003-11-10 TW TW092131351A patent/TW200418799A/zh unknown
- 2003-11-10 AR ARP030104130A patent/AR042023A1/es not_active Application Discontinuation
- 2003-11-10 HN HN2003000353A patent/HN2003000353A/es unknown
- 2003-11-10 PE PE2003001135A patent/PE20040672A1/es not_active Application Discontinuation
-
2005
- 2005-05-11 EC EC2005005789A patent/ECSP055789A/es unknown
- 2005-05-11 MA MA28277A patent/MA27491A1/fr unknown
- 2005-06-08 CO CO05055462A patent/CO5580824A2/es not_active Application Discontinuation
- 2005-06-09 NO NO20052797A patent/NO20052797L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003276201A1 (en) | 2004-06-03 |
| MA27491A1 (fr) | 2005-08-01 |
| CO5580824A2 (es) | 2005-11-30 |
| PE20040672A1 (es) | 2004-10-29 |
| HRP20050529A2 (en) | 2006-08-31 |
| KR20050074571A (ko) | 2005-07-18 |
| ECSP055789A (es) | 2005-08-11 |
| NO20052797D0 (no) | 2005-06-09 |
| EP1575919A1 (en) | 2005-09-21 |
| AR042023A1 (es) | 2005-06-08 |
| CA2505361A1 (en) | 2004-05-27 |
| BR0316191A (pt) | 2005-09-27 |
| UY28072A1 (es) | 2004-06-30 |
| NO20052797L (no) | 2005-06-09 |
| HN2003000353A (es) | 2003-11-23 |
| JP2006514110A (ja) | 2006-04-27 |
| PL376993A1 (pl) | 2006-01-23 |
| US20060089371A1 (en) | 2006-04-27 |
| WO2004043926A1 (en) | 2004-05-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW200418799A (en) | Phenyl or heteroaryl amino alkane derivatives | |
| JP4688498B2 (ja) | Jakインヒビターとしてのヘテロアリール−ピリミジン誘導体 | |
| TW523511B (en) | Pharmaceutical composition comprising substituted imidazole compounds and process for preparing compounds | |
| AU2013261129B2 (en) | Compounds and compositions for inhibiting the activity of ABL1, ABL2 and BCR-ABL1 | |
| CA2507100C (en) | 2,4,6-trisubstituted pyrimidines as phosphotidylinositol (pi) 3-kinase inhibitors and their use in the treatment of cancer | |
| ES2536216T3 (es) | Composiciones y métodos para modular la ruta de señalización de Wnt | |
| JP2010229154A (ja) | Jakインヒビターおよび他のプロテインキナーゼインヒビターとしての組成物の使用 | |
| BRPI0720635A2 (pt) | Compostos orgânicos e seus usos | |
| CA2463823A1 (en) | Aminobenzamide derivatives as glycogen synthase kinase 3.beta. inhibitors | |
| TWI465439B (zh) | 三氮唑衍生物或其鹽 | |
| US11352352B2 (en) | Aminopyrimidine compound, preparation method therefor and use thereof | |
| TW201004936A (en) | Organic compounds | |
| TW201300360A (zh) | 做為jak激酶調節劑之菸鹼醯胺 | |
| TW200902010A (en) | Anthranilamide inhibitors of aurora kinase | |
| TW200526598A (en) | Pyrimidine derivatives | |
| TW201026681A (en) | New(3-oxo)pyridazin-4-ylurea derivatives | |
| CA2724077A1 (en) | Amide compound | |
| WO2013108754A1 (ja) | ピラジンカルボキサミド化合物 | |
| WO2010058846A1 (ja) | 4,6-ジアミノニコチンアミド化合物 | |
| SI9520080A (sl) | Substituirane pirimidinske spojine in njihova uporaba | |
| TW200400190A (en) | Pyrimidine compounds | |
| CA2949785A1 (en) | Mth1 inhibitors for treatment of cancer | |
| AU2011346670B2 (en) | Glucagon receptor modulators | |
| WO2020135210A1 (zh) | 取代芳基化合物及其制备方法和用途 | |
| AU2005311452A1 (en) | Triazole compounds suitable for treating disorders that respond to modulaiont of the dopamine D3 receptor |