SK4699A3 - Arylcycloalkane carboxylic esters, their use, pharmaceutical compositions and preparation - Google Patents

Arylcycloalkane carboxylic esters, their use, pharmaceutical compositions and preparation Download PDF

Info

Publication number: SK4699A3
Authority: SK; Slovakia
Prior art keywords: phenyl; acid; compound; formula; prepared
Prior art date: 1996-07-29

Application number

SK46-99A

Other languages

English (en)

Slovak (sk)

Inventor

Eva Akerblom

Martin Haraldsson

Rolf Johansson

Katarina Beierlein

Birger Sjoberg

Erik Ringberg

Birgitta Weinz

Original Assignee

Pharmacia & Upjohn Ab

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.)

1996-07-29

Filing date

1997-07-23

Publication date

2000-04-10

1996-07-29 Priority claimed from SE9602889A external-priority patent/SE9602889D0/xx

1996-07-29 Priority claimed from SE9602888A external-priority patent/SE9602888D0/xx

1996-07-29 Priority claimed from SE9602887A external-priority patent/SE9602887D0/xx

1996-07-29 Priority claimed from SE9602890A external-priority patent/SE9602890D0/xx

1997-07-23 Application filed by Pharmacia & Upjohn Ab filed Critical Pharmacia & Upjohn Ab

2000-04-10 Publication of SK4699A3 publication Critical patent/SK4699A3/sk

Links

238000002360 preparation method Methods 0.000 title claims abstract description 20
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 13
150000001733 carboxylic acid esters Chemical class 0.000 title description 2
239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 239
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 119
229910052799 carbon Inorganic materials 0.000 claims abstract description 103
125000000217 alkyl group Chemical group 0.000 claims abstract description 57
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 32
239000001257 hydrogen Substances 0.000 claims abstract description 31
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 16
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 13
229920006395 saturated elastomer Polymers 0.000 claims abstract description 13
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 12
206010046543 Urinary incontinence Diseases 0.000 claims abstract description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 10
125000005605 benzo group Chemical group 0.000 claims abstract description 9
125000004122 cyclic group Chemical group 0.000 claims abstract description 9
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 4
-1 N-methyl-4-piperidyl Chemical group 0.000 claims description 126
239000002253 acid Substances 0.000 claims description 96
238000000034 method Methods 0.000 claims description 52
238000006243 chemical reaction Methods 0.000 claims description 23
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
150000002431 hydrogen Chemical class 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000004494 ethyl ester group Chemical group 0.000 claims description 14
239000013543 active substance Substances 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
150000001721 carbon Chemical group 0.000 claims description 12
208000011580 syndromic disease Diseases 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
230000007794 irritation Effects 0.000 claims description 8
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 7
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 6
150000001930 cyclobutanes Chemical group 0.000 claims description 6
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
STHHLVCQSLRQNI-UHFFFAOYSA-N 1-azabicyclo[3.2.1]octane Chemical compound C1C2CCN1CCC2 STHHLVCQSLRQNI-UHFFFAOYSA-N 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 5
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
JVCBVWTTXCNJBJ-UHFFFAOYSA-N 1-azabicyclo[2.2.1]heptane Chemical compound C1CC2CCN1C2 JVCBVWTTXCNJBJ-UHFFFAOYSA-N 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 3
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 3
XLRPYZSEQKXZAA-OCAPTIKFSA-N tropane Chemical compound C1CC[C@H]2CC[C@@H]1N2C XLRPYZSEQKXZAA-OCAPTIKFSA-N 0.000 claims description 3
229930004006 tropane Natural products 0.000 claims description 3
FMEHIMDNLRASDU-UHFFFAOYSA-N 1-azabicyclo[3.3.1]nonane Chemical compound C1CCN2CCCC1C2 FMEHIMDNLRASDU-UHFFFAOYSA-N 0.000 claims description 2
150000001934 cyclohexanes Chemical group 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
ASUQYWCXZRNVRW-UHFFFAOYSA-N 4-azabicyclo[3.2.1]octane Chemical compound C1C2CCC1NCC2 ASUQYWCXZRNVRW-UHFFFAOYSA-N 0.000 claims 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
150000003053 piperidines Chemical class 0.000 claims 2
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
230000003287 optical effect Effects 0.000 claims 1
208000002551 irritable bowel syndrome Diseases 0.000 abstract description 9
125000001475 halogen functional group Chemical group 0.000 abstract 1
125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 237
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 118
229910052757 nitrogen Inorganic materials 0.000 description 89
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 77
239000000741 silica gel Substances 0.000 description 77
229910002027 silica gel Inorganic materials 0.000 description 77
239000003480 eluent Substances 0.000 description 69
239000012043 crude product Substances 0.000 description 56
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
239000011541 reaction mixture Substances 0.000 description 44
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 42
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
235000019439 ethyl acetate Nutrition 0.000 description 41
239000000126 substance Substances 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
239000000203 mixture Substances 0.000 description 36
150000002148 esters Chemical class 0.000 description 35
IVLICPVPXWEGCA-UHFFFAOYSA-N 3-quinuclidinol Chemical compound C1C[C@@H]2C(O)C[N@]1CC2 IVLICPVPXWEGCA-UHFFFAOYSA-N 0.000 description 31
238000004458 analytical method Methods 0.000 description 31
239000012044 organic layer Substances 0.000 description 28
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000000047 product Substances 0.000 description 24
229910000104 sodium hydride Inorganic materials 0.000 description 24
ZYWUVGFIXPNBDL-UHFFFAOYSA-N n,n-diisopropylaminoethanol Chemical compound CC(C)N(C(C)C)CCO ZYWUVGFIXPNBDL-UHFFFAOYSA-N 0.000 description 23
VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000003208 petroleum Substances 0.000 description 19
239000000243 solution Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
239000010410 layer Substances 0.000 description 17
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
229940093476 ethylene glycol Drugs 0.000 description 14
239000006185 dispersion Substances 0.000 description 13
239000002480 mineral oil Substances 0.000 description 13
235000010446 mineral oil Nutrition 0.000 description 13
239000002904 solvent Substances 0.000 description 13
SVSUIHVKXBTVBI-UHFFFAOYSA-N 1-phenylcyclobutane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CCC1 SVSUIHVKXBTVBI-UHFFFAOYSA-N 0.000 description 12
238000007792 addition Methods 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
JHZRNLRTNIDFKG-UHFFFAOYSA-N 1-phenylcyclobutane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCC1 JHZRNLRTNIDFKG-UHFFFAOYSA-N 0.000 description 10
150000001732 carboxylic acid derivatives Chemical class 0.000 description 10
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 10
CZCLTIDPEQAYOD-UHFFFAOYSA-N 1-thiophen-2-ylcyclopentane-1-carboxylic acid Chemical compound C=1C=CSC=1C1(C(=O)O)CCCC1 CZCLTIDPEQAYOD-UHFFFAOYSA-N 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
239000003921 oil Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
RKPYIONWLOSCEL-UHFFFAOYSA-N 1-thiophen-3-ylcyclopentane-1-carboxylic acid Chemical compound C1=CSC=C1C1(C(=O)O)CCCC1 RKPYIONWLOSCEL-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 8
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
229960004484 carbachol Drugs 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
208000035475 disorder Diseases 0.000 description 7
238000001035 drying Methods 0.000 description 7
150000004678 hydrides Chemical class 0.000 description 7
210000003681 parotid gland Anatomy 0.000 description 7
239000011734 sodium Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
210000003932 urinary bladder Anatomy 0.000 description 7
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
229910004373 HOAc Inorganic materials 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
230000001078 anti-cholinergic effect Effects 0.000 description 6
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 6
125000004043 oxo group Chemical group O=* 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000000605 extraction Methods 0.000 description 5
230000004044 response Effects 0.000 description 5
239000000725 suspension Substances 0.000 description 5
BAUWRHPMUVYFOD-UHFFFAOYSA-N 1-methylpiperidin-4-ol Chemical compound CN1CCC(O)CC1 BAUWRHPMUVYFOD-UHFFFAOYSA-N 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 4
229940013085 2-diethylaminoethanol Drugs 0.000 description 4
229930003347 Atropine Natural products 0.000 description 4
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 4
229960000396 atropine Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
230000027455 binding Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
230000000694 effects Effects 0.000 description 4
LJWKFGGDMBPPAZ-UHFFFAOYSA-N ethoxyethane;toluene Chemical compound CCOCC.CC1=CC=CC=C1 LJWKFGGDMBPPAZ-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
NOYKUYNVZHTPCI-UHFFFAOYSA-N 1-phenylcyclopentane-1-carbonyl chloride Chemical compound C=1C=CC=CC=1C1(C(=O)Cl)CCCC1 NOYKUYNVZHTPCI-UHFFFAOYSA-N 0.000 description 3
RHPCYZLXNNRRMB-UHFFFAOYSA-N 1-phenylcyclopentane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCC1 RHPCYZLXNNRRMB-UHFFFAOYSA-N 0.000 description 3
CLSRUFAQOVMBBX-UHFFFAOYSA-N 3,3-dimethyl-1-phenylcyclobutane-1-carboxylic acid Chemical compound C1C(C)(C)CC1(C(O)=O)C1=CC=CC=C1 CLSRUFAQOVMBBX-UHFFFAOYSA-N 0.000 description 3
AGTQEBDKTIZDCC-UHFFFAOYSA-N 4-methoxy-1-phenylcyclohexane-1-carboxylic acid Chemical compound C1CC(OC)CCC1(C(O)=O)C1=CC=CC=C1 AGTQEBDKTIZDCC-UHFFFAOYSA-N 0.000 description 3
GLXVJOPRMXBHSI-UHFFFAOYSA-N 4-oxo-1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCC(=O)CC1 GLXVJOPRMXBHSI-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000037396 body weight Effects 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
238000004587 chromatography analysis Methods 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
230000008602 contraction Effects 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
229910052731 fluorine Inorganic materials 0.000 description 3
239000012458 free base Substances 0.000 description 3
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239000003795 chemical substances by application Substances 0.000 description 1
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239000000812 cholinergic antagonist Substances 0.000 description 1
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125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
HXGBXQDTNZMWGS-RUZDIDTESA-N darifenacin Chemical compound C=1C=CC=CC=1C([C@H]1CN(CCC=2C=C3CCOC3=CC=2)CC1)(C(=O)N)C1=CC=CC=C1 HXGBXQDTNZMWGS-RUZDIDTESA-N 0.000 description 1
229960002677 darifenacin Drugs 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
CURUTKGFNZGFSE-UHFFFAOYSA-N dicyclomine Chemical compound C1CCCCC1C1(C(=O)OCCN(CC)CC)CCCCC1 CURUTKGFNZGFSE-UHFFFAOYSA-N 0.000 description 1
229960002777 dicycloverine Drugs 0.000 description 1
KPPLIMDJGPOMAL-UHFFFAOYSA-K dipotassium;sodium;phosphate Chemical compound [Na+].[K+].[K+].[O-]P([O-])([O-])=O KPPLIMDJGPOMAL-UHFFFAOYSA-K 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
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238000002224 dissection Methods 0.000 description 1
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238000006266 etherification reaction Methods 0.000 description 1
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125000005843 halogen group Chemical group 0.000 description 1
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230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002513 implantation Methods 0.000 description 1
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238000007918 intramuscular administration Methods 0.000 description 1
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238000001990 intravenous administration Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
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SHFZCNVCHWMUCS-UHFFFAOYSA-N methyl 1-(4-nitrophenyl)cyclobutane-1-carboxylate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C1(C(=O)OC)CCC1 SHFZCNVCHWMUCS-UHFFFAOYSA-N 0.000 description 1
JJHCLPDHYBSSHC-UHFFFAOYSA-N methyl 2-methyl-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1C JJHCLPDHYBSSHC-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000472 muscarinic agonist Substances 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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239000000025 natural resin Substances 0.000 description 1
239000003958 nerve gas Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
FDJSESZWPWMLEC-UHFFFAOYSA-N nonane Chemical compound CCCCCCCC[CH2+] FDJSESZWPWMLEC-UHFFFAOYSA-N 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940100692 oral suspension Drugs 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 1
229960004633 pirenzepine Drugs 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 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
239000008057 potassium phosphate buffer Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000008213 purified water Substances 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
230000002048 spasmolytic effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229960001032 trihexyphenidyl Drugs 0.000 description 1
CYHOMWAPJJPNMW-JIGDXULJSA-N tropine Chemical compound C1[C@@H](O)C[C@H]2CC[C@@H]1N2C CYHOMWAPJJPNMW-JIGDXULJSA-N 0.000 description 1
230000002485 urinary effect Effects 0.000 description 1
230000035899 viability Effects 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000005303 weighing Methods 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
- C07D409/12—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 chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/10—Drugs for disorders of the urinary system of the bladder
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C219/12—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the hydroxy groups esterified by a carboxylic acid having the esterifying carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Hydrogenated Pyridines (AREA)
Medicinal Preparation (AREA)

SK46-99A 1996-07-29 1997-07-23 Arylcycloalkane carboxylic esters, their use, pharmaceutical compositions and preparation SK4699A3 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
SE9602889A SE9602889D0 (sv)	1996-07-29	1996-07-29	Carboxylic esters, their use and preparation
SE9602888A SE9602888D0 (sv)	1996-07-29	1996-07-29	Carboxylic esters, their use and preparation
SE9602887A SE9602887D0 (sv)	1996-07-29	1996-07-29	Carboxylic esters, their use and preparation
SE9602890A SE9602890D0 (sv)	1996-07-29	1996-07-29	Carboxylic esters, their use and preparation
PCT/SE1997/001310 WO1998004517A1 (en)	1996-07-29	1997-07-23	Arylcycloalkane carboxylic esters, their use, pharmaceutical compositions and preparation

Publications (1)

Publication Number	Publication Date
SK4699A3 true SK4699A3 (en)	2000-04-10

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ID=27484794

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK46-99A SK4699A3 (en)	1996-07-29	1997-07-23	Arylcycloalkane carboxylic esters, their use, pharmaceutical compositions and preparation

Country Status (17)

Country	Link
US (1)	US6124354A (de)
EP (1)	EP0923536A1 (de)
JP (1)	JP2000515881A (de)
KR (1)	KR20000029703A (de)
CN (1)	CN1226886A (de)
AU (1)	AU724563B2 (de)
BG (1)	BG103207A (de)
BR (1)	BR9710614A (de)
CA (1)	CA2261692A1 (de)
EE (1)	EE9900034A (de)
IL (1)	IL128096A0 (de)
NO (1)	NO990335L (de)
NZ (1)	NZ333798A (de)
PL (1)	PL331384A1 (de)
SK (1)	SK4699A3 (de)
TR (1)	TR199900185T2 (de)
WO (1)	WO1998004517A1 (de)

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PE20020547A1 (es)	2000-10-24	2002-06-12	Upjohn Co	Uso de la tolterodina en tratamientos del asma
MXPA04003806A (es) *	2001-11-05	2005-04-08	Upjohn Co	Aerosol antimuscarinico.
AU2004206846B2 (en) *	2003-01-16	2009-05-28	University Of Rochester	Quaternary antimuscarinic compounds for the treatment of bladder diseases
WO2008059239A1 (en) *	2006-11-14	2008-05-22	Astrazeneca Ab	Novel compounds 514
TW200825084A (en)	2006-11-14	2008-06-16	Astrazeneca Ab	New compounds 521
BRPI0912657A2 (pt) *	2008-05-13	2016-01-26	Astrazeneca Ab	produto farmacêutico compreendendo um antagonista de receptor muscarínico e um agonista beta2-adrenorreceptor
EA017627B1 (ru)	2008-05-13	2013-01-30	Астразенека Аб	Хинуклидиновые производные в качестве антагонистов мускаринового м3 рецептора
WO2012145234A2 (en) *	2011-04-21	2012-10-26	Emory University	Cyclopropyl derivatives and methods of use
MA37975B2 (fr)	2012-09-11	2021-03-31	Genzyme Corp	Inhibiteurs de synthase de glucosylcéramide
TW201517906A (zh)	2013-07-25	2015-05-16	Almirall Sa	含有ｍａｂａ化合物和皮質類固醇之組合
TW201617343A (zh) *	2014-09-26	2016-05-16	阿爾米雷爾有限公司	具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物
CN106083615B (zh) *	2016-06-08	2019-03-08	山东省药学科学院	一种盐酸环喷托酯的制备方法
US11274100B2 (en)	2017-06-21	2022-03-15	Daiichi Sankyo Company, Limited	EP300/CREBBP inhibitor
CN114040762A (zh)	2019-02-04	2022-02-11	建新公司	使用葡糖神经酰胺合酶(gcs)的抑制剂治疗纤毛疾病
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JP2023512366A (ja)	2020-02-03	2023-03-27	ジェンザイム・コーポレーション	リソソーム蓄積性疾患と関連する神経学的症状を処置するための方法
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1997
- 1997-07-23 JP JP10508739A patent/JP2000515881A/ja active Pending
- 1997-07-23 US US09/230,164 patent/US6124354A/en not_active Expired - Fee Related
- 1997-07-23 EE EEP199900034A patent/EE9900034A/xx unknown
- 1997-07-23 EP EP97934832A patent/EP0923536A1/de not_active Withdrawn
- 1997-07-23 AU AU37905/97A patent/AU724563B2/en not_active Ceased
- 1997-07-23 PL PL97331384A patent/PL331384A1/xx unknown
- 1997-07-23 IL IL12809697A patent/IL128096A0/xx unknown
- 1997-07-23 TR TR1999/00185T patent/TR199900185T2/xx unknown
- 1997-07-23 SK SK46-99A patent/SK4699A3/sk unknown
- 1997-07-23 NZ NZ333798A patent/NZ333798A/xx unknown
- 1997-07-23 KR KR1019997000803A patent/KR20000029703A/ko not_active Withdrawn
- 1997-07-23 BR BR9710614-3A patent/BR9710614A/pt unknown
- 1997-07-23 WO PCT/SE1997/001310 patent/WO1998004517A1/en not_active Ceased
- 1997-07-23 CN CN97196892A patent/CN1226886A/zh active Pending
- 1997-07-23 CA CA002261692A patent/CA2261692A1/en not_active Abandoned
1999
- 1999-01-25 NO NO990335A patent/NO990335L/no not_active Application Discontinuation
- 1999-02-25 BG BG103207A patent/BG103207A/xx unknown

Also Published As

Publication number	Publication date
WO1998004517A1 (en)	1998-02-05
CA2261692A1 (en)	1998-02-05
KR20000029703A (ko)	2000-05-25
PL331384A1 (en)	1999-07-05
US6124354A (en)	2000-09-26
IL128096A0 (en)	1999-11-30
BR9710614A (pt)	2000-01-11
NO990335L (no)	1999-03-29
AU3790597A (en)	1998-02-20
CN1226886A (zh)	1999-08-25
EP0923536A1 (de)	1999-06-23
JP2000515881A (ja)	2000-11-28
BG103207A (en)	1999-10-29
NZ333798A (en)	2000-08-25
EE9900034A (et)	1999-08-16
AU724563B2 (en)	2000-09-28
TR199900185T2 (xx)	1999-04-21
NO990335D0 (no)	1999-01-25

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