CA2632279A1 - Composes de sulfonamide heteroaromatiques - Google Patents

Composes de sulfonamide heteroaromatiques Download PDF

Info

Publication number: CA2632279A1
Authority: CA; Canada
Prior art keywords: beta; trien; carboxylate; hydroxyoestra; sulphamoyl
Prior art date: 2005-11-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002632279A

Other languages

English (en)

Inventor

Ralf Wyrwa

Reinhard Nubbemeyer

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Pharma AG

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-11-30

Filing date

2006-11-27

Publication date

2007-06-07

2006-11-27 Application filed by Individual filed Critical Individual

2007-06-07 Publication of CA2632279A1 publication Critical patent/CA2632279A1/fr

Status Abandoned legal-status Critical Current

Links

229940002612 prodrug Drugs 0.000 title claims abstract description 23
239000000651 prodrug Substances 0.000 title claims abstract description 23
229940124530 sulfonamide Drugs 0.000 title claims abstract description 9
-1 Heteroaromatic sulfonamide Chemical class 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 43
239000003814 drug Substances 0.000 claims abstract description 25
229940079593 drug Drugs 0.000 claims abstract description 16
238000004519 manufacturing process Methods 0.000 claims abstract description 8
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
239000011664 nicotinic acid Substances 0.000 claims description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
238000011321 prophylaxis Methods 0.000 claims description 7
FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 7
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
201000010099 disease Diseases 0.000 claims description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
239000000583 progesterone congener Substances 0.000 claims description 4
150000003431 steroids Chemical class 0.000 claims description 4
229930192474 thiophene Natural products 0.000 claims description 4
WWYNJERNGUHSAO-XUDSTZEESA-N (+)-Norgestrel Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 WWYNJERNGUHSAO-XUDSTZEESA-N 0.000 claims description 3
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
239000003098 androgen Substances 0.000 claims description 3
239000003418 antiprogestin Substances 0.000 claims description 3
201000008275 breast carcinoma Diseases 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
229960003309 dienogest Drugs 0.000 claims description 3
AZFLJNIPTRTECV-FUMNGEBKSA-N dienogest Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)([C@](CC3)(O)CC#N)CC3)C3=C21 AZFLJNIPTRTECV-FUMNGEBKSA-N 0.000 claims description 3
229930182833 estradiol Natural products 0.000 claims description 3
239000000262 estrogen Substances 0.000 claims description 3
230000035558 fertility Effects 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
229960004400 levonorgestrel Drugs 0.000 claims description 3
229940053934 norethindrone Drugs 0.000 claims description 3
VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
239000002379 progesterone receptor modulator Substances 0.000 claims description 3
230000003637 steroidlike Effects 0.000 claims description 3
229960003604 testosterone Drugs 0.000 claims description 3
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
IEXUMDBQLIVNHZ-YOUGDJEHSA-N (8s,11r,13r,14s,17s)-11-[4-(dimethylamino)phenyl]-17-hydroxy-17-(3-hydroxypropyl)-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(O)CCCO)[C@@]2(C)C1 IEXUMDBQLIVNHZ-YOUGDJEHSA-N 0.000 claims description 2
201000009273 Endometriosis Diseases 0.000 claims description 2
206010058359 Hypogonadism Diseases 0.000 claims description 2
208000026935 allergic disease Diseases 0.000 claims description 2
GJMNAFGEUJBOCE-MEQIQULJSA-N asoprisnil Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@]([C@]3(C2)C)(COC)OC)=CC=C(\C=N\O)C=C1 GJMNAFGEUJBOCE-MEQIQULJSA-N 0.000 claims description 2
229950003620 asoprisnil Drugs 0.000 claims description 2
150000001733 carboxylic acid esters Chemical class 0.000 claims description 2
238000003776 cleavage reaction Methods 0.000 claims description 2
METQSPRSQINEEU-UHFFFAOYSA-N dihydrospirorenone Natural products CC12CCC(C3(CCC(=O)C=C3C3CC33)C)C3C1C1CC1C21CCC(=O)O1 METQSPRSQINEEU-UHFFFAOYSA-N 0.000 claims description 2
229960004845 drospirenone Drugs 0.000 claims description 2
METQSPRSQINEEU-HXCATZOESA-N drospirenone Chemical compound C([C@]12[C@H]3C[C@H]3[C@H]3[C@H]4[C@@H]([C@]5(CCC(=O)C=C5[C@@H]5C[C@@H]54)C)CC[C@@]31C)CC(=O)O2 METQSPRSQINEEU-HXCATZOESA-N 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
238000002657 hormone replacement therapy Methods 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
230000002757 inflammatory effect Effects 0.000 claims description 2
229960003248 mifepristone Drugs 0.000 claims description 2
VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims description 2
229950011093 onapristone Drugs 0.000 claims description 2
230000007017 scission Effects 0.000 claims description 2
229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 claims description 2
238000002560 therapeutic procedure Methods 0.000 claims 4
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
YSGQGNQWBLYHPE-UHFFFAOYSA-N 17-hydroxy-7,13-dimethyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-3-one Chemical compound C1CC2(C)C(O)CCC2C2C(C)CC3=CC(=O)CCC3C21 YSGQGNQWBLYHPE-UHFFFAOYSA-N 0.000 claims 2
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 claims 2
UYSRSLSTXYYNEW-UHFFFAOYSA-N NS(=O)(=O)S(O)(=O)=O Chemical compound NS(=O)(=O)S(O)(=O)=O UYSRSLSTXYYNEW-UHFFFAOYSA-N 0.000 claims 2
229960003473 androstanolone Drugs 0.000 claims 2
239000003054 catalyst Substances 0.000 claims 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims 2
PROQIPRRNZUXQM-UHFFFAOYSA-N (16alpha,17betaOH)-Estra-1,3,5(10)-triene-3,16,17-triol Natural products OC1=CC=C2C3CCC(C)(C(C(O)C4)O)C4C3CCC2=C1 PROQIPRRNZUXQM-UHFFFAOYSA-N 0.000 claims 1
201000009030 Carcinoma Diseases 0.000 claims 1
229940030486 androgens Drugs 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
230000008878 coupling Effects 0.000 claims 1
238000010168 coupling process Methods 0.000 claims 1
238000005859 coupling reaction Methods 0.000 claims 1
PROQIPRRNZUXQM-ZXXIGWHRSA-N estriol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H]([C@H](O)C4)O)[C@@H]4[C@@H]3CCC2=C1 PROQIPRRNZUXQM-ZXXIGWHRSA-N 0.000 claims 1
229960000890 hydrocortisone Drugs 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
239000002207 metabolite Substances 0.000 claims 1
229960004719 nandrolone Drugs 0.000 claims 1
REACBNMPQDINOF-YBBIQVIJSA-N nandrolone cyclotate Chemical compound C1CC(C)(C=C2)CCC12C(=O)O[C@H]1CC[C@H]2[C@H](CCC=3[C@@H]4CCC(=O)C=3)[C@@H]4CC[C@@]21C REACBNMPQDINOF-YBBIQVIJSA-N 0.000 claims 1
210000002307 prostate Anatomy 0.000 claims 1
GZONDLFHZLDEFX-UHFFFAOYSA-N sulfamoylformyl chloride Chemical compound NS(=O)(=O)C(Cl)=O GZONDLFHZLDEFX-UHFFFAOYSA-N 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 3
108090000790 Enzymes Proteins 0.000 abstract description 3
150000003456 sulfonamides Chemical class 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 17
238000005160 1H NMR spectroscopy Methods 0.000 description 16
239000000126 substance Substances 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
210000003743 erythrocyte Anatomy 0.000 description 9
210000002381 plasma Anatomy 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000003826 tablet Substances 0.000 description 8
DGCASRZGTMMLIS-UHFFFAOYSA-N 2-sulfamoylpyridine-3-carboxylic acid Chemical compound NS(=O)(=O)C1=NC=CC=C1C(O)=O DGCASRZGTMMLIS-UHFFFAOYSA-N 0.000 description 7
150000007942 carboxylates Chemical class 0.000 description 6
238000011282 treatment Methods 0.000 description 6
229910052786 argon Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
RPKYZDOXCVNXBE-UHFFFAOYSA-N 5-sulfamoylpyridine-3-carboxylic acid Chemical compound NS(=O)(=O)C1=CN=CC(C(O)=O)=C1 RPKYZDOXCVNXBE-UHFFFAOYSA-N 0.000 description 4
KUGDGAKDFIXCAL-UHFFFAOYSA-N 6-sulfamoylpyridine-3-carboxylic acid Chemical compound NS(=O)(=O)C1=CC=C(C(O)=O)C=N1 KUGDGAKDFIXCAL-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
OQIQSTLJSLGHID-WNWIJWBNSA-N aflatoxin B1 Chemical compound C=1([C@@H]2C=CO[C@@H]2OC=1C=C(C1=2)OC)C=2OC(=O)C2=C1CCC2=O OQIQSTLJSLGHID-WNWIJWBNSA-N 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
GHCQNEIFBBBMQB-UHFFFAOYSA-N 5-methylpyridine-3-sulfonic acid Chemical compound CC1=CN=CC(S(O)(=O)=O)=C1 GHCQNEIFBBBMQB-UHFFFAOYSA-N 0.000 description 3
101150041968 CDC13 gene Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000002390 heteroarenes Chemical class 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
235000000346 sugar Nutrition 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
239000001828 Gelatine Substances 0.000 description 2
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 description 2
150000007513 acids Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
125000005647 linker group Chemical group 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
238000002156 mixing Methods 0.000 description 2
239000002777 nucleoside Substances 0.000 description 2
239000001267 polyvinylpyrrolidone Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 1
MRCKRGSNLOHYRA-UHFFFAOYSA-N (2-nitrophenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1[N+]([O-])=O MRCKRGSNLOHYRA-UHFFFAOYSA-N 0.000 description 1
125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical class CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 description 1
LSWSLKPCPFDKHR-UHFFFAOYSA-N 2-bromo-5-sulfamoylthiophene-3-carboxylic acid Chemical compound NS(=O)(=O)C1=CC(C(O)=O)=C(Br)S1 LSWSLKPCPFDKHR-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical class BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical class BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
XBWGBXKCBYUTFT-UHFFFAOYSA-N 2-ethyl-5-sulfamoylthiophene-3-carboxylic acid Chemical compound CCC=1SC(S(N)(=O)=O)=CC=1C(O)=O XBWGBXKCBYUTFT-UHFFFAOYSA-N 0.000 description 1
JCCCMAAJYSNBPR-UHFFFAOYSA-N 2-ethylthiophene Chemical class CCC1=CC=CS1 JCCCMAAJYSNBPR-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
GJOHLWZHWQUKAU-UHFFFAOYSA-N 5-azaniumylpentan-2-yl-(6-methoxyquinolin-8-yl)azanium;dihydrogen phosphate Chemical compound OP(O)(O)=O.OP(O)(O)=O.N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 GJOHLWZHWQUKAU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
229920002261 Corn starch Polymers 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
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 1
229920000084 Gum arabic Polymers 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
238000012404 In vitro experiment Methods 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
235000019759 Maize starch Nutrition 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 1
229960000571 acetazolamide Drugs 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 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
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
230000001028 anti-proliverative effect Effects 0.000 description 1
239000003430 antimalarial agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960001169 brivudine Drugs 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
238000011088 calibration curve Methods 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940096529 carboxypolymethylene Drugs 0.000 description 1
229940081734 cellulose acetate phthalate Drugs 0.000 description 1
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
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 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
150000001885 cortisol derivatives Chemical class 0.000 description 1
229940109275 cyclamate Drugs 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
HJKVPZJVBHWFCQ-BDXSIMOUSA-N estra-1,3,5(10)-trien-3-ol Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 HJKVPZJVBHWFCQ-BDXSIMOUSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000007941 film coated tablet Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
ODZBBRURCPAEIQ-PIXDULNESA-N helpin Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 ODZBBRURCPAEIQ-PIXDULNESA-N 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 description 1
229960004171 hydroxychloroquine Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229940125721 immunosuppressive agent Drugs 0.000 description 1
CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 1
229960001936 indinavir Drugs 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000004388 isoflavanoid group Chemical group 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
201000004792 malaria Diseases 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
229960001962 mefloquine Drugs 0.000 description 1
229910000372 mercury(II) sulfate Inorganic materials 0.000 description 1
QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 description 1
229960000884 nelfinavir Drugs 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
125000003835 nucleoside group Chemical group 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229940075065 polyvinyl acetate Drugs 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
229960005179 primaquine Drugs 0.000 description 1
239000000047 product Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
201000001514 prostate carcinoma Diseases 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000004208 shellac Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
235000013874 shellac Nutrition 0.000 description 1
229940113147 shellac Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000002700 tablet coating Substances 0.000 description 1
238000009492 tablet coating Methods 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000002110 toxicologic effect Effects 0.000 description 1
231100000027 toxicology Toxicity 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
229960002555 zidovudine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- 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
- A61K31/64—Sulfonylureas, e.g. glibenclamide, tolbutamide, chlorpropamide
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/5685—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
- 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
- A61K31/59—Compounds containing 9, 10- seco- cyclopenta[a]hydrophenanthrene ring systems
- 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
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
- 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
- A61P35/00—Antineoplastic agents
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J33/00—Normal steroids having a sulfur-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Epidemiology (AREA)
Gynecology & Obstetrics (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Pulmonology (AREA)
Diabetes (AREA)
Pregnancy & Childbirth (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CA002632279A 2005-11-30 2006-11-27 Composes de sulfonamide heteroaromatiques Abandoned CA2632279A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE102005057421A DE102005057421A1 (de)	2005-11-30	2005-11-30	Heteroaromatische Sulfonamid-Prodrugs
DE102005057421.1		2005-11-30
PCT/EP2006/011727 WO2007062875A1 (fr)	2005-11-30	2006-11-27	Composes de sulfonamide heteroaromatiques

Publications (1)

Publication Number	Publication Date
CA2632279A1 true CA2632279A1 (fr)	2007-06-07

Family

ID=37875507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002632279A Abandoned CA2632279A1 (fr)	2005-11-30	2006-11-27	Composes de sulfonamide heteroaromatiques

Country Status (14)

Country	Link
EP (1)	EP1959964A1 (fr)
JP (1)	JP2009517425A (fr)
KR (1)	KR20080074197A (fr)
CN (1)	CN101321535A (fr)
AU (1)	AU2006319381A1 (fr)
BR (1)	BRPI0619214A2 (fr)
CA (1)	CA2632279A1 (fr)
DE (1)	DE102005057421A1 (fr)
EA (1)	EA200801209A1 (fr)
EC (1)	ECSP088488A (fr)
IL (1)	IL191563A0 (fr)
NO (1)	NO20082916L (fr)
WO (1)	WO2007062875A1 (fr)
ZA (1)	ZA200805660B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN101987102A (zh) *	2009-08-05	2011-03-23	天津金耀集团有限公司	一种糖皮质激素杂芳香基氨磺酰基羧酸酯的眼用抗炎组合物
CN101987104A (zh) *	2009-08-05	2011-03-23	天津金耀集团有限公司	一种杂芳香基氨磺酰基羧酸酯碳酸酐酶抑制剂的眼用组合物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1593609A (en) *	1978-01-31	1981-07-22	Christiaens Sa A	Pyridine sulfonamides
DE10027887A1 (de) *	2000-05-31	2001-12-13	Jenapharm Gmbh	Verbindungen mit einer Sulfonamidgruppe und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
US6355666B1 (en) *	2000-06-23	2002-03-12	Medinox, Inc.	Protected forms of pharmacologically active agents and uses therefor
AR053845A1 (es) *	2005-04-15	2007-05-23	Tibotec Pharm Ltd	5-tiazolilmetil[(1s,2r)-3-[[(2-amino-6-benzoxazolil)sulfonil)](2-metilpropil)amino]-2-hidroxi-1-(fenilmetil)propil]carbamato como mejorador de farmacos metabolizados por el citocromo p450

2005
- 2005-11-30 DE DE102005057421A patent/DE102005057421A1/de not_active Ceased
2006
- 2006-11-27 KR KR1020087015778A patent/KR20080074197A/ko not_active Withdrawn
- 2006-11-27 CA CA002632279A patent/CA2632279A1/fr not_active Abandoned
- 2006-11-27 EA EA200801209A patent/EA200801209A1/ru unknown
- 2006-11-27 EP EP06829355A patent/EP1959964A1/fr not_active Withdrawn
- 2006-11-27 AU AU2006319381A patent/AU2006319381A1/en not_active Abandoned
- 2006-11-27 CN CNA2006800450153A patent/CN101321535A/zh active Pending
- 2006-11-27 WO PCT/EP2006/011727 patent/WO2007062875A1/fr not_active Ceased
- 2006-11-27 JP JP2008542679A patent/JP2009517425A/ja active Pending
- 2006-11-27 BR BRPI0619214-9A patent/BRPI0619214A2/pt not_active Application Discontinuation
2008
- 2008-05-20 IL IL191563A patent/IL191563A0/en unknown
- 2008-05-30 EC EC2008008488A patent/ECSP088488A/es unknown
- 2008-06-27 ZA ZA200805660A patent/ZA200805660B/xx unknown
- 2008-06-27 NO NO20082916A patent/NO20082916L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
EA200801209A1 (ru)	2008-12-30
WO2007062875A1 (fr)	2007-06-07
ECSP088488A (es)	2008-06-30
IL191563A0 (en)	2009-08-03
EP1959964A1 (fr)	2008-08-27
JP2009517425A (ja)	2009-04-30
AU2006319381A1 (en)	2007-06-07
NO20082916L (no)	2008-06-27
WO2007062875B1 (fr)	2007-08-09
DE102005057421A1 (de)	2007-05-31
KR20080074197A (ko)	2008-08-12
CN101321535A (zh)	2008-12-10
ZA200805660B (en)	2009-11-25
BRPI0619214A2 (pt)	2011-09-20

Legal Events

Date	Code	Title	Description
2010-11-29	FZDE	Discontinued

Publication	Publication Date	Title
JP6861703B2 (ja)	2021-04-21	Ｔｇｒ５修飾物質およびその使用方法
CA1319362C (fr)	1993-06-22	Derives androstenedione substitues en 4, et procede pour leur preparation
US20050288267A1 (en)	2005-12-29	Estradiol prodrugs
NO303450B1 (no)	1998-07-13	AnalogifremgangsmÕte for fremstilling av terapeutisk aktive gallesyrederivater
JP2911553B2 (ja)	1999-06-23	１１β―アリール―４―エストレン、その製法、中間生成物及び新規化合物を含有する抗ゲスタゲン及び抗グルココルチコイド作用を有する製薬学的製済
US10246481B2 (en)	2019-04-02	Bile acid derivatives and methods for synthesis and use
US8492570B2 (en)	2013-07-23	2-substituted estra-1,3,5(10)-triene-3-yl sulfamate with an anti-tumor action
JP2003517436A (ja)	2003-05-27	１９−ノルアンドロスタン系列の１４，１５−シクロプロパノステロイド、その製造法および該化合物を含有する製薬学的調製剤
HU177333B (en)	1981-09-28	Process for producing gona-4,9-bracket-10-bracket closeddienes
AU713341B2 (en)	1999-12-02	3-substituted-d-homo-1,3,5,(10)-estratriene derivatives
CA1310957C (fr)	1992-12-01	Derives 10-alkynylestrene et procede pour leur preparation
EP0434571A2 (fr)	1991-06-26	Nouveaux produits stéroides comportant, en position 10, un radical éthyle substitué, leur procédé de préparation, application comme médicament de l'un de ces produits et les compositions pharmaceutiques le renfermant
KR100450854B1 (ko)	2004-12-16	α-17치환체가없는신규의프레그난유도체,이들의의약용도,제조방법,및이의중간체및관련화합물
NZ240925A (en)	1995-02-24	Heterocyclically-substituted fluoromethyl benzene derivatives, preparation and pharmaceutical compositions thereof
CA2632279A1 (fr)	2007-06-07	Composes de sulfonamide heteroaromatiques
US20070135399A1 (en)	2007-06-14	Heteroaromatic sulphonamide prodrugs
MX2008007039A (en)	2008-09-02	Heteroaromatic sulfonamide prodrugs
US20070123500A1 (en)	2007-05-31	Prodrugs of ERbeta-selective substances, processes for their preparation and pharmaceutical compositions comprising these compounds
CA2632272A1 (fr)	2007-06-07	Promedicaments de sulfonate de sulfamoyle
HU197028B (en)	1989-02-28	Process for producing 6alpha-amino- and -azidosteroids and pharmaceuticals with aromatase inhibiting effect comprising the same
NO313413B1 (no)	2002-09-30	Hydrokinonderivat, anvendelse derav og farmasöytisk preparat
US20070135375A1 (en)	2007-06-14	Sulfamoyl sulfonate prodrugs
IE46562B1 (en)	1983-07-27	17a-acetylene derivatives of androst-4-ene,processes for preparing them and pharmaceutical compositions containing them
CZ216895A3 (en)	1996-04-17	Novel derivatives of 3-hydroxyanthranilic acid, process and intermediates of their preparation, novel pharmaceutical preparations and their use
NO840092L (no)	1984-07-13	Fremgangsmaate for fremstilling av substituerte karboksy-tiazolo(3,2-a)pyrimidin-derivater