FI78080C - Foerfarande foer framstaellning av bensotiazolsulfonamidderivat, vilka aer anvaendbara vid behandling av foerhoejt intraokulaert tryck. - Google Patents
Foerfarande foer framstaellning av bensotiazolsulfonamidderivat, vilka aer anvaendbara vid behandling av foerhoejt intraokulaert tryck. Download PDFInfo
- Publication number
- FI78080C FI78080C FI822464A FI822464A FI78080C FI 78080 C FI78080 C FI 78080C FI 822464 A FI822464 A FI 822464A FI 822464 A FI822464 A FI 822464A FI 78080 C FI78080 C FI 78080C
- Authority
- FI
- Finland
- Prior art keywords
- sulfamoyl
- benzothiazolyl
- mol
- alkyl
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 4
- SDYMYAFSQACTQP-UHFFFAOYSA-N 1,3-benzothiazole-2-sulfonamide Chemical class C1=CC=C2SC(S(=O)(=O)N)=NC2=C1 SDYMYAFSQACTQP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims 1
- 125000000565 sulfonamide group Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 239000005457 ice water Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- -1 for example Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- NOOBQTYVTDBXTL-UHFFFAOYSA-N 6-hydroxy-1,3-benzothiazole-2-sulfonamide Chemical compound C1=C(O)C=C2SC(S(=O)(=O)N)=NC2=C1 NOOBQTYVTDBXTL-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 230000004410 intraocular pressure Effects 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 208000010412 Glaucoma Diseases 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 102000003846 Carbonic anhydrases Human genes 0.000 description 6
- 108090000209 Carbonic anhydrases Proteins 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- NIAKACXIACUKAT-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) benzoate Chemical compound C1=C2SC(S(=O)(=O)N)=NC2=CC=C1OC(=O)C1=CC=CC=C1 NIAKACXIACUKAT-UHFFFAOYSA-N 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000002876 beta blocker Substances 0.000 description 4
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 4
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 3
- ONLKWCLNLGKXRT-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) acetate Chemical compound CC(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 ONLKWCLNLGKXRT-UHFFFAOYSA-N 0.000 description 3
- ADXZIFWDMLTXKC-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 ADXZIFWDMLTXKC-UHFFFAOYSA-N 0.000 description 3
- VCBZXNUEICJWCV-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) octanoate Chemical compound CCCCCCCC(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 VCBZXNUEICJWCV-UHFFFAOYSA-N 0.000 description 3
- GTIUYAOJHKKPJX-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) prop-2-enoate Chemical compound C1=C(OC(=O)C=C)C=C2SC(S(=O)(=O)N)=NC2=C1 GTIUYAOJHKKPJX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 3
- 229940093471 ethyl oleate Drugs 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 229960001416 pilocarpine Drugs 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- AUYIAPXFWGZBHX-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) 2,2,2-trifluoroacetate Chemical compound C1=C(OC(=O)C(F)(F)F)C=C2SC(S(=O)(=O)N)=NC2=C1 AUYIAPXFWGZBHX-UHFFFAOYSA-N 0.000 description 2
- MTEUZRMFJMJGDP-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) 2-(4-chlorophenyl)acetate Chemical compound C1=C2SC(S(=O)(=O)N)=NC2=CC=C1OC(=O)CC1=CC=C(Cl)C=C1 MTEUZRMFJMJGDP-UHFFFAOYSA-N 0.000 description 2
- YOHTWEQBOHRRPZ-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) 3-phenylprop-2-enoate Chemical compound C1=C2SC(S(=O)(=O)N)=NC2=CC=C1OC(=O)C=CC1=CC=CC=C1 YOHTWEQBOHRRPZ-UHFFFAOYSA-N 0.000 description 2
- XFPLVUDHBNYLTL-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) hexanoate Chemical compound CCCCCC(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 XFPLVUDHBNYLTL-UHFFFAOYSA-N 0.000 description 2
- QQYSMJUATUAFIG-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) propanoate Chemical compound CCC(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 QQYSMJUATUAFIG-UHFFFAOYSA-N 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 2
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- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 239000001856 Ethyl cellulose Substances 0.000 description 2
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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- RQNLCRINVQPVLZ-UHFFFAOYSA-N NS(C1=C(C(O)=O)C(C2=NC(C=CC=C3)=C3S2)=CC(Cl)=C1)(=O)=O Chemical compound NS(C1=C(C(O)=O)C(C2=NC(C=CC=C3)=C3S2)=CC(Cl)=C1)(=O)=O RQNLCRINVQPVLZ-UHFFFAOYSA-N 0.000 description 2
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- 229920002125 Sokalan® Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- FAZPZNCEAZRGPY-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 FAZPZNCEAZRGPY-UHFFFAOYSA-N 0.000 description 1
- MEBIIUBUTCZSJM-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) 2-phenylacetate Chemical compound C1=C2SC(S(=O)(=O)N)=NC2=CC=C1OC(=O)CC1=CC=CC=C1 MEBIIUBUTCZSJM-UHFFFAOYSA-N 0.000 description 1
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- CMXVSVCNGADSSO-UHFFFAOYSA-N (2-sulfamoyl-1,3-benzothiazol-6-yl) cyclohexanecarboxylate Chemical compound C1=C2SC(S(=O)(=O)N)=NC2=CC=C1OC(=O)C1CCCCC1 CMXVSVCNGADSSO-UHFFFAOYSA-N 0.000 description 1
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- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 description 1
- 241000206576 Chondrus Species 0.000 description 1
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- 241000206672 Gelidium Species 0.000 description 1
- 241000223783 Glaucoma Species 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
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- 229920001612 Hydroxyethyl starch Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 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
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
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- MKRNVBXERAPZOP-UHFFFAOYSA-N Starch acetate Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OC(C)=O)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 MKRNVBXERAPZOP-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
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- VJDDQSBNUHLBTD-GGWOSOGESA-N [(e)-but-2-enoyl] (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC(=O)\C=C\C VJDDQSBNUHLBTD-GGWOSOGESA-N 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- JOHUAELJNSBTGS-UHFFFAOYSA-N cyclohexanecarbonyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC(=O)C1CCCCC1 JOHUAELJNSBTGS-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-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
- OUZWUKMCLIBBOG-UHFFFAOYSA-N ethoxzolamide Chemical compound CCOC1=CC=C2N=C(S(N)(=O)=O)SC2=C1 OUZWUKMCLIBBOG-UHFFFAOYSA-N 0.000 description 1
- 229960004667 ethyl cellulose Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940014259 gelatin Drugs 0.000 description 1
- PKHMTIRCAFTBDS-UHFFFAOYSA-N hexanoyl hexanoate Chemical compound CCCCCC(=O)OC(=O)CCCCC PKHMTIRCAFTBDS-UHFFFAOYSA-N 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000001341 hydroxy propyl starch Substances 0.000 description 1
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- 229940071826 hydroxyethyl cellulose Drugs 0.000 description 1
- 229940050526 hydroxyethylstarch Drugs 0.000 description 1
- 235000013828 hydroxypropyl starch Nutrition 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- LSACYLWPPQLVSM-UHFFFAOYSA-N isobutyric acid anhydride Chemical compound CC(C)C(=O)OC(=O)C(C)C LSACYLWPPQLVSM-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 208000018769 loss of vision Diseases 0.000 description 1
- 231100000864 loss of vision Toxicity 0.000 description 1
- 230000000936 membranestabilizing effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000003733 optic disk Anatomy 0.000 description 1
- 230000008807 pathological lesion Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229960000292 pectin Drugs 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009885 systemic effect Effects 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 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
- VJDDQSBNUHLBTD-UHFFFAOYSA-N trans-crotonic acid-anhydride Natural products CC=CC(=O)OC(=O)C=CC VJDDQSBNUHLBTD-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 229920003169 water-soluble polymer Polymers 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
- C07D277/80—Sulfur atoms attached to a second hetero atom to a nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28247081A | 1981-07-13 | 1981-07-13 | |
| US28247081 | 1981-07-13 | ||
| US35240082A | 1982-02-25 | 1982-02-25 | |
| US35240082 | 1982-02-25 |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI822464A0 FI822464A0 (fi) | 1982-07-09 |
| FI822464L FI822464L (fi) | 1983-01-14 |
| FI78080B FI78080B (fi) | 1989-02-28 |
| FI78080C true FI78080C (fi) | 1989-06-12 |
Family
ID=26961471
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI822464A FI78080C (fi) | 1981-07-13 | 1982-07-09 | Foerfarande foer framstaellning av bensotiazolsulfonamidderivat, vilka aer anvaendbara vid behandling av foerhoejt intraokulaert tryck. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0070239B1 (enExample) |
| AR (1) | AR241136A1 (enExample) |
| AU (1) | AU556363B2 (enExample) |
| CA (1) | CA1185980A (enExample) |
| DE (1) | DE3264033D1 (enExample) |
| DK (1) | DK312082A (enExample) |
| ES (1) | ES513831A0 (enExample) |
| FI (1) | FI78080C (enExample) |
| GR (1) | GR76527B (enExample) |
| IE (1) | IE53868B1 (enExample) |
| IL (1) | IL66238A0 (enExample) |
| NO (1) | NO157538C (enExample) |
| NZ (1) | NZ201157A (enExample) |
| PT (1) | PT75229B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5095026A (en) * | 1983-02-04 | 1992-03-10 | University Of Iowa Research Foundation | Prodrugs of carbonic anhydrase inhibitors |
| US4500538A (en) * | 1983-03-14 | 1985-02-19 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| US4499103A (en) * | 1983-03-17 | 1985-02-12 | Merck & Co., Inc. | Benzothiazole-2-sulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| US4472417A (en) * | 1983-04-22 | 1984-09-18 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| US4470991A (en) * | 1983-04-22 | 1984-09-11 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| US4472418A (en) * | 1983-04-22 | 1984-09-18 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| US4456599A (en) * | 1983-04-22 | 1984-06-26 | Merck & Co., Inc. | Benzothiazolesulfonamide derivatives for the topical treatment of elevated intraocular pressure |
| ES8600752A1 (es) * | 1983-06-20 | 1985-10-16 | Merck & Co Inc | Un procedimiento para la preparacion de nuevos derivados de tiosulfonamida. |
| NZ208444A (en) * | 1983-06-20 | 1987-08-31 | Merck & Co Inc | 2-thiophene derivatives and pharmaceutical compositions |
| US4544667A (en) * | 1984-02-09 | 1985-10-01 | Merck & Co., Inc. | 2-Sulfamoylbenzo[b]furan derivatives for the treatment of elevated intraocular pressure |
| DE3576498D1 (de) * | 1984-03-14 | 1990-04-19 | Merck & Co Inc | 2-sulfamoyl-1h-indole-derivate zur behandlung von hohem intraocularem druck. |
| US5059613A (en) * | 1990-03-19 | 1991-10-22 | Research Corporation Technologies, Inc. | Topically active ocular benzothiazole sulfonamide carbonic anhydrase inhibitors |
| US5519040A (en) * | 1994-04-29 | 1996-05-21 | Allergan | Substituted thiazole sulfonamides as antiglaucoma agents |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2595334A (en) * | 1950-04-08 | 1952-05-06 | American Cyanamid Co | Benzothiazolesulfonamides and method of preparing the same |
| US2868800A (en) * | 1954-10-13 | 1959-01-13 | Upjohn Co | 6-ethoxybenzothiazole-2-sulfonamide |
-
1982
- 1982-06-08 AR AR289937A patent/AR241136A1/es active
- 1982-07-05 NZ NZ201157A patent/NZ201157A/en unknown
- 1982-07-06 IL IL66238A patent/IL66238A0/xx not_active IP Right Cessation
- 1982-07-07 GR GR68682A patent/GR76527B/el unknown
- 1982-07-09 FI FI822464A patent/FI78080C/fi not_active IP Right Cessation
- 1982-07-09 CA CA000407023A patent/CA1185980A/en not_active Expired
- 1982-07-09 AU AU85775/82A patent/AU556363B2/en not_active Ceased
- 1982-07-09 ES ES513831A patent/ES513831A0/es active Granted
- 1982-07-09 EP EP82401299A patent/EP0070239B1/en not_active Expired
- 1982-07-09 DE DE8282401299T patent/DE3264033D1/de not_active Expired
- 1982-07-12 PT PT75229A patent/PT75229B/pt not_active IP Right Cessation
- 1982-07-12 NO NO822410A patent/NO157538C/no unknown
- 1982-07-12 IE IE1668/82A patent/IE53868B1/en unknown
- 1982-07-12 DK DK312082A patent/DK312082A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO157538C (no) | 1988-04-06 |
| EP0070239A1 (en) | 1983-01-19 |
| AU556363B2 (en) | 1986-10-30 |
| AR241136A1 (es) | 1991-11-29 |
| PT75229A (en) | 1982-08-01 |
| FI822464A0 (fi) | 1982-07-09 |
| GR76527B (enExample) | 1984-08-10 |
| PT75229B (en) | 1985-10-04 |
| IE53868B1 (en) | 1989-03-29 |
| NZ201157A (en) | 1985-02-28 |
| DE3264033D1 (en) | 1985-07-11 |
| CA1185980A (en) | 1985-04-23 |
| AR241136A2 (es) | 1991-11-29 |
| AU8577582A (en) | 1983-01-20 |
| NO822410L (no) | 1983-01-14 |
| EP0070239B1 (en) | 1985-06-05 |
| NO157538B (no) | 1987-12-28 |
| ES8400417A1 (es) | 1983-11-01 |
| FI78080B (fi) | 1989-02-28 |
| IL66238A0 (en) | 1982-11-30 |
| DK312082A (da) | 1983-01-14 |
| ES513831A0 (es) | 1983-11-01 |
| FI822464L (fi) | 1983-01-14 |
| IE821668L (en) | 1983-01-13 |
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Owner name: MERCK & CO., INC. |