NZ578698A - Substituted gamma lactams as therapeutic agents - Google Patents
Substituted gamma lactams as therapeutic agentsInfo
- Publication number
- NZ578698A NZ578698A NZ578698A NZ57869808A NZ578698A NZ 578698 A NZ578698 A NZ 578698A NZ 578698 A NZ578698 A NZ 578698A NZ 57869808 A NZ57869808 A NZ 57869808A NZ 578698 A NZ578698 A NZ 578698A
- Authority
- NZ
- New Zealand
- Prior art keywords
- another embodiment
- compound
- phenyl
- pharmaceutically acceptable
- acceptable salt
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 7
- 150000003953 γ-lactams Chemical class 0.000 title abstract description 3
- 229940124597 therapeutic agent Drugs 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000000203 mixture Substances 0.000 claims abstract description 22
- 208000010412 Glaucoma Diseases 0.000 claims abstract description 15
- 210000004209 hair Anatomy 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 8
- 230000003648 hair appearance Effects 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 235000019439 ethyl acetate Nutrition 0.000 claims description 10
- 230000004410 intraocular pressure Effects 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000741 silica gel Substances 0.000 claims description 6
- 229910002027 silica gel Inorganic materials 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000012074 organic phase Substances 0.000 claims description 5
- 206010030043 Ocular hypertension Diseases 0.000 claims description 4
- 239000012267 brine Substances 0.000 claims description 4
- 238000004587 chromatography analysis Methods 0.000 claims description 4
- 230000001631 hypertensive effect Effects 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 238000001727 in vivo Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 230000036439 ocular surface hyperemia Effects 0.000 claims 6
- 241000282472 Canis lupus familiaris Species 0.000 claims 3
- 241000282693 Cercopithecidae Species 0.000 claims 3
- 229940125904 compound 1 Drugs 0.000 claims 2
- -1 linear Chemical class 0.000 description 131
- 125000001424 substituent group Chemical group 0.000 description 22
- 229940002612 prodrug Drugs 0.000 description 20
- 239000000651 prodrug Substances 0.000 description 20
- 239000002207 metabolite Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 3
- KSVAISBWHHQWSP-NRFANRHFSA-N 2-hydroxyethyl 5-[3-[(2s)-1-(4-hexylphenyl)-5-oxopyrrolidin-2-yl]propyl]thiophene-2-carboxylate Chemical compound C1=CC(CCCCCC)=CC=C1N1C(=O)CC[C@@H]1CCCC1=CC=C(C(=O)OCCO)S1 KSVAISBWHHQWSP-NRFANRHFSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 201000002862 Angle-Closure Glaucoma Diseases 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 210000002159 anterior chamber Anatomy 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000000068 chlorophenyl group Chemical group 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- 208000002177 Cataract Diseases 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 201000001326 acute closed-angle glaucoma Diseases 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002066 eicosanoids Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000001207 fluorophenyl group Chemical group 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003568 thioethers Chemical group 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- HOBJEFOCIRXQKH-SCSAIBSYSA-N (5r)-5-(hydroxymethyl)pyrrolidin-2-one Chemical compound OC[C@H]1CCC(=O)N1 HOBJEFOCIRXQKH-SCSAIBSYSA-N 0.000 description 1
- ZQUDZYWZGZOAJB-UHFFFAOYSA-N 2-(5-carboxythiophen-2-yl)ethyl-triphenylphosphanium;bromide Chemical compound [Br-].S1C(C(=O)O)=CC=C1CC[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZQUDZYWZGZOAJB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- WXWCSPFQIXPFLD-YMXDCFFPSA-N 5-[3-[(2s)-1-[4-(1-hydroxyhexyl)phenyl]-5-oxopyrrolidin-2-yl]propyl]thiophene-2-carboxylic acid Chemical compound C1=CC(C(O)CCCCC)=CC=C1N1C(=O)CC[C@@H]1CCCC1=CC=C(C(O)=O)S1 WXWCSPFQIXPFLD-YMXDCFFPSA-N 0.000 description 1
- 229940082496 Adrenoreceptor antagonist Drugs 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 206010018325 Congenital glaucomas Diseases 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 206010012565 Developmental glaucoma Diseases 0.000 description 1
- 208000031969 Eye Hemorrhage Diseases 0.000 description 1
- 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 1
- 206010067684 Iris bombe Diseases 0.000 description 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 206010068960 Narrow anterior chamber angle Diseases 0.000 description 1
- 208000022873 Ocular disease Diseases 0.000 description 1
- 206010030348 Open-Angle Glaucoma Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229960001948 caffeine Drugs 0.000 description 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 201000005667 central retinal vein occlusion Diseases 0.000 description 1
- 201000005682 chronic closed-angle glaucoma Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 230000010339 dilation Effects 0.000 description 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical group [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910001410 inorganic ion Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 208000018769 loss of vision Diseases 0.000 description 1
- 231100000864 loss of vision Toxicity 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000000116 mitigating effect Effects 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000004644 retinal vein occlusion Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 210000001585 trabecular meshwork Anatomy 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88741507P | 2007-01-31 | 2007-01-31 | |
| PCT/US2008/052318 WO2008094912A2 (en) | 2007-01-31 | 2008-01-29 | Substituted gamma lactams as therapeutic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ578698A true NZ578698A (en) | 2012-04-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ578698A NZ578698A (en) | 2007-01-31 | 2008-01-29 | Substituted gamma lactams as therapeutic agents |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7960381B2 (enExample) |
| EP (1) | EP2121672B1 (enExample) |
| JP (1) | JP5566692B2 (enExample) |
| KR (1) | KR101561706B1 (enExample) |
| CN (1) | CN101595106B (enExample) |
| AU (1) | AU2008210559B2 (enExample) |
| BR (1) | BRPI0808377B8 (enExample) |
| CA (1) | CA2676291C (enExample) |
| MX (1) | MX2009008039A (enExample) |
| NZ (1) | NZ578698A (enExample) |
| WO (1) | WO2008094912A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8377984B2 (en) * | 2008-01-29 | 2013-02-19 | Allergan, Inc. | Substituted gamma lactams as therapeutic agents |
| AU2009239381A1 (en) * | 2008-04-24 | 2009-10-29 | Allergan, Inc. | Substituted gamma lactams as therapeutic agents |
| EP2291368B1 (en) * | 2008-04-24 | 2012-12-19 | Allergan, Inc. | Substituted gamma lactams as therapeutic agents |
| CA2722456A1 (en) | 2008-04-24 | 2009-10-29 | Allergan, Inc. | Substituted arylcyclopentenes as prostaglandin ep2 agonists |
| BRPI0912342A2 (pt) * | 2008-05-09 | 2015-10-06 | Allergan Inc | tiazolidinonas, oxazolidinonas substituídas terapêuticas, e compostos relacionados |
| EP2285775B1 (en) * | 2008-05-20 | 2017-03-22 | Allergan, Inc. | Lactams and their use in the treatment of inter alia ocular hypertension or baldness |
Family Cites Families (8)
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| WO2003008377A1 (en) * | 2001-07-16 | 2003-01-30 | F. Hoffmann-La Roche Ag | Prostaglandin analogues_as ep4 receptor agonists |
| CA2466517A1 (en) * | 2001-11-05 | 2003-05-15 | Allergan, Inc. | .omega.-cycloalkyl 17-heteroaryl prostaglandin e2 analogs as ep2-receptor agonists |
| NZ535024A (en) * | 2002-03-05 | 2006-10-27 | Ono Pharmaceutical Co | 8-azaprostaglandin derivative compound and agent comprising the compound as active ingredient |
| US6573294B1 (en) * | 2002-05-14 | 2003-06-03 | Allergan, Inc. | 8-azaprostaglandin analogs as agents for lowering intraocular pressure |
| CA2483555A1 (en) * | 2002-06-10 | 2003-12-18 | Applied Research Systems Ars Holding N.V. | Gamma lactams as prostaglandin agonists and use thereof |
| US7091231B2 (en) * | 2004-12-10 | 2006-08-15 | Allergan, Inc. | 12-Aryl prostaglandin analogs |
| RU2412933C2 (ru) | 2005-03-10 | 2011-02-27 | Аллерган, Инк. | Замещенные гамма-лактамы в качестве терапевтических агентов |
| EP1996546B1 (en) | 2006-03-20 | 2014-11-26 | Allergan, Inc. | Substituted gamma lactams as prostaglandin ep2 agonists |
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2008
- 2008-01-29 CN CN200880003507.5A patent/CN101595106B/zh not_active Expired - Fee Related
- 2008-01-29 JP JP2009548391A patent/JP5566692B2/ja not_active Expired - Fee Related
- 2008-01-29 CA CA2676291A patent/CA2676291C/en not_active Expired - Fee Related
- 2008-01-29 EP EP08728470.9A patent/EP2121672B1/en not_active Not-in-force
- 2008-01-29 BR BRPI0808377A patent/BRPI0808377B8/pt not_active IP Right Cessation
- 2008-01-29 AU AU2008210559A patent/AU2008210559B2/en not_active Ceased
- 2008-01-29 MX MX2009008039A patent/MX2009008039A/es active IP Right Grant
- 2008-01-29 WO PCT/US2008/052318 patent/WO2008094912A2/en not_active Ceased
- 2008-01-29 KR KR1020097017970A patent/KR101561706B1/ko not_active Expired - Fee Related
- 2008-01-29 US US12/524,803 patent/US7960381B2/en active Active
- 2008-01-29 NZ NZ578698A patent/NZ578698A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2121672A2 (en) | 2009-11-25 |
| CN101595106A (zh) | 2009-12-02 |
| JP5566692B2 (ja) | 2014-08-06 |
| EP2121672B1 (en) | 2014-12-10 |
| CA2676291C (en) | 2017-11-28 |
| BRPI0808377B8 (pt) | 2021-05-25 |
| US20100093729A1 (en) | 2010-04-15 |
| CN101595106B (zh) | 2014-05-07 |
| AU2008210559B2 (en) | 2014-03-06 |
| CA2676291A1 (en) | 2008-08-07 |
| WO2008094912A3 (en) | 2008-10-09 |
| WO2008094912B1 (en) | 2008-11-20 |
| JP2010516817A (ja) | 2010-05-20 |
| KR20090104905A (ko) | 2009-10-06 |
| WO2008094912A2 (en) | 2008-08-07 |
| KR101561706B1 (ko) | 2015-10-19 |
| US7960381B2 (en) | 2011-06-14 |
| AU2008210559A1 (en) | 2008-08-07 |
| BRPI0808377A2 (pt) | 2014-07-08 |
| BRPI0808377B1 (pt) | 2020-01-21 |
| MX2009008039A (es) | 2009-08-18 |
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