NO314354B1 - Enantiomerrene estere, fremgangsmåte for deres fremstilling og deres anvendelse i legemidler - Google Patents

Enantiomerrene estere, fremgangsmåte for deres fremstilling og deres anvendelse i legemidler Download PDF

Info

Publication number: NO314354B1
Authority: NO; Norway
Prior art keywords: general formula; methyl; dimethyl; oxy; pyrrolidinium
Prior art date: 1996-11-11

Application number

NO19991056A

Other languages

English (en)

Norwegian (no)

Other versions

NO991056L (no

NO991056D0 (no

Inventor

Guenter Lambrecht

Michael Manfred Elgert

Sittah Czeche

Magali Waelbroeck

Original Assignee

Mutschler Ernst

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.)

1996-11-11

Filing date

1999-03-03

Publication date

2003-03-10

1999-03-03 Application filed by Mutschler Ernst filed Critical Mutschler Ernst

1999-03-03 Publication of NO991056D0 publication Critical patent/NO991056D0/no

1999-05-11 Publication of NO991056L publication Critical patent/NO991056L/no

2003-03-10 Publication of NO314354B1 publication Critical patent/NO314354B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 20
150000002148 esters Chemical class 0.000 title claims description 17
238000000034 method Methods 0.000 title claims description 15
239000003814 drug Substances 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 5
239000002253 acid Substances 0.000 claims abstract description 12
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
150000001450 anions Chemical class 0.000 claims abstract description 5
125000002619 bicyclic group Chemical group 0.000 claims abstract description 3
125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
-1 cyclopentyl-hydroxyphenylacetyl Chemical group 0.000 claims description 82
150000001875 compounds Chemical class 0.000 claims description 40
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 17
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 13
125000005843 halogen group Chemical group 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
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 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
210000001035 gastrointestinal tract Anatomy 0.000 claims description 6
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
230000000414 obstructive effect Effects 0.000 claims description 6
208000023504 respiratory system disease Diseases 0.000 claims description 6
210000002460 smooth muscle Anatomy 0.000 claims description 6
206010006458 Bronchitis chronic Diseases 0.000 claims description 5
150000001414 amino alcohols Chemical class 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
206010006451 bronchitis Diseases 0.000 claims description 5
208000007451 chronic bronchitis Diseases 0.000 claims description 5
208000030603 inherited susceptibility to asthma Diseases 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
208000007101 Muscle Cramp Diseases 0.000 claims description 4
208000005392 Spasm Diseases 0.000 claims description 4
238000002425 crystallisation Methods 0.000 claims description 4
230000008025 crystallization Effects 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
229940100198 alkylating agent Drugs 0.000 claims description 3
239000002168 alkylating agent Substances 0.000 claims description 3
125000001302 tertiary amino group Chemical group 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
229940126601 medicinal product Drugs 0.000 claims description 2
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
125000003118 aryl group Chemical group 0.000 abstract description 2
229910052757 nitrogen Inorganic materials 0.000 abstract description 2
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 2
125000001475 halogen functional group Chemical group 0.000 abstract 2
125000001072 heteroaryl group Chemical group 0.000 abstract 1
102220047090 rs6152 Human genes 0.000 description 21
101150013553 CD40 gene Proteins 0.000 description 14
102100040245 Tumor necrosis factor receptor superfamily member 5 Human genes 0.000 description 14
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
229910052740 iodine Inorganic materials 0.000 description 11
238000010494 dissociation reaction Methods 0.000 description 10
230000005593 dissociations Effects 0.000 description 10
238000000926 separation method Methods 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 8
102000017925 CHRM3 Human genes 0.000 description 8
101150060249 CHRM3 gene Proteins 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 8
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
229960002462 glycopyrronium bromide Drugs 0.000 description 8
230000000144 pharmacologic effect Effects 0.000 description 8
238000005956 quaternization reaction Methods 0.000 description 8
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 6
229940095064 tartrate Drugs 0.000 description 6
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000047 product Substances 0.000 description 5
230000002048 spasmolytic effect Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
239000000812 cholinergic antagonist Substances 0.000 description 4
230000003993 interaction Effects 0.000 description 4
229940102396 methyl bromide Drugs 0.000 description 4
230000002445 parasympatholytic effect Effects 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 3
102000017926 CHRM2 Human genes 0.000 description 3
101150012960 Chrm2 gene Proteins 0.000 description 3
FEWJPZIEWOKRBE-JCYAYHJZSA-M L-tartrate(1-) Chemical compound OC(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-M 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000028327 secretion Effects 0.000 description 3
239000000243 solution Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
FLVFPAIGVBQGET-RXMQYKEDSA-N (3r)-1-methylpyrrolidin-3-ol Chemical compound CN1CC[C@@H](O)C1 FLVFPAIGVBQGET-RXMQYKEDSA-N 0.000 description 2
FLVFPAIGVBQGET-YFKPBYRVSA-N (3s)-1-methylpyrrolidin-3-ol Chemical compound CN1CC[C@H](O)C1 FLVFPAIGVBQGET-YFKPBYRVSA-N 0.000 description 2
125000006059 1,1-dimethyl-2-butenyl group Chemical group 0.000 description 2
XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 2
241000700199 Cavia porcellus Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000033228 biological regulation Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000011835 investigation Methods 0.000 description 2
PMGPEWXWCQNWCP-UHFFFAOYSA-N methyl 2-(6-cyclohexyl-6-hydroxycyclohexa-2,4-dien-1-yl)acetate Chemical compound COC(=O)CC1C=CC=CC1(O)C1CCCCC1 PMGPEWXWCQNWCP-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
125000006730 (C2-C5) alkynyl group Chemical group 0.000 description 1
125000006079 1,1,2-trimethyl-2-propenyl group Chemical group 0.000 description 1
125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
125000006060 1,1-dimethyl-3-butenyl group Chemical group 0.000 description 1
GARJMFRQLMUUDD-UHFFFAOYSA-N 1,1-dimethylpyrrolidin-1-ium Chemical group C[N+]1(C)CCCC1 GARJMFRQLMUUDD-UHFFFAOYSA-N 0.000 description 1
125000005919 1,2,2-trimethylpropyl group Chemical group 0.000 description 1
125000006062 1,2-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
125000006063 1,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
125000005918 1,2-dimethylbutyl group Chemical group 0.000 description 1
125000006065 1,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006066 1,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
125000006080 1-ethyl-1-methyl-2-propenyl group Chemical group 0.000 description 1
125000006082 1-ethyl-2-methyl-2-propenyl group Chemical group 0.000 description 1
125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
125000006075 1-ethyl-3-butenyl group Chemical group 0.000 description 1
125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
125000006048 1-methyl-2-pentenyl group Chemical group 0.000 description 1
125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
125000006052 1-methyl-3-pentenyl group Chemical group 0.000 description 1
125000006055 1-methyl-4-pentenyl group Chemical group 0.000 description 1
125000006067 2,2-dimethyl-3-butenyl group Chemical group 0.000 description 1
125000006069 2,3-dimethyl-2-butenyl group Chemical group 0.000 description 1
125000006070 2,3-dimethyl-3-butenyl group Chemical group 0.000 description 1
VIUBPJBHBABDOJ-UHFFFAOYSA-N 2-(6-cyclohexyl-6-hydroxycyclohexa-2,4-dien-1-yl)acetic acid Chemical class OC(=O)CC1C=CC=CC1(O)C1CCCCC1 VIUBPJBHBABDOJ-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
125000006076 2-ethyl-1-butenyl group Chemical group 0.000 description 1
125000006077 2-ethyl-2-butenyl group Chemical group 0.000 description 1
125000006078 2-ethyl-3-butenyl group Chemical group 0.000 description 1
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
125000006049 2-methyl-2-pentenyl group Chemical group 0.000 description 1
125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
125000006053 2-methyl-3-pentenyl group Chemical group 0.000 description 1
125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
125000005916 2-methylpentyl group Chemical group 0.000 description 1
125000006024 2-pentenyl group Chemical group 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
125000006054 3-methyl-3-pentenyl group Chemical group 0.000 description 1
125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 1
125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005917 3-methylpentyl group Chemical group 0.000 description 1
125000006042 4-hexenyl group Chemical group 0.000 description 1
125000006051 4-methyl-2-pentenyl group Chemical group 0.000 description 1
125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000006058 4-methyl-4-pentenyl group Chemical group 0.000 description 1
125000006043 5-hexenyl group Chemical group 0.000 description 1
NBDAHKQJXVLAID-UHFFFAOYSA-N 5-nitroisophthalic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC([N+]([O-])=O)=C1 NBDAHKQJXVLAID-UHFFFAOYSA-N 0.000 description 1
208000028048 Accommodation disease Diseases 0.000 description 1
229920000858 Cyclodextrin Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
239000001358 L(+)-tartaric acid Substances 0.000 description 1
FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
RVOLLAQWKVFTGE-UHFFFAOYSA-N Pyridostigmine Chemical compound CN(C)C(=O)OC1=CC=C[N+](C)=C1 RVOLLAQWKVFTGE-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
YTRNSQPXEDGWMR-UHFFFAOYSA-N alpha-Cyclohexylmandelic acid Chemical class C=1C=CC=CC=1C(O)(C(=O)O)C1CCCCC1 YTRNSQPXEDGWMR-UHFFFAOYSA-N 0.000 description 1
239000012491 analyte Substances 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
210000000013 bile duct Anatomy 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000008499 blood brain barrier function Effects 0.000 description 1
210000001218 blood-brain barrier Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
239000007853 buffer solution Substances 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
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
230000008859 change Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001142 circular dichroism spectrum Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
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
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
238000011161 development Methods 0.000 description 1
230000010339 dilation Effects 0.000 description 1
238000009826 distribution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000001261 hydroxy acids Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000008095 long lasting therapeutic effect Effects 0.000 description 1
NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical group C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
SEAGJNIQYGDOEE-UHFFFAOYSA-N methyl 2-(6-cyclopentyl-6-hydroxycyclohexa-2,4-dien-1-yl)acetate Chemical compound COC(=O)CC1C=CC=CC1(O)C1CCCC1 SEAGJNIQYGDOEE-UHFFFAOYSA-N 0.000 description 1
230000003551 muscarinic effect Effects 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960002362 neostigmine Drugs 0.000 description 1
LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
230000002276 neurotropic effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000001747 pupil Anatomy 0.000 description 1
230000010344 pupil dilation Effects 0.000 description 1
229960002290 pyridostigmine Drugs 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
210000003296 saliva Anatomy 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000008054 signal transmission Effects 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
210000004243 sweat Anatomy 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000000825 ultraviolet detection Methods 0.000 description 1
210000003932 urinary bladder Anatomy 0.000 description 1
210000004291 uterus Anatomy 0.000 description 1
210000001177 vas deferen Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010626 work up procedure 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- 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
- 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
- C07D211/36—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 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
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5

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)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Neurology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrrole Compounds (AREA)
Hydrogenated Pyridines (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO19991056A 1996-11-11 1999-03-03 Enantiomerrene estere, fremgangsmåte for deres fremstilling og deres anvendelse i legemidler NO314354B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
AT197396		1996-11-11
PCT/AT1997/000245 WO1998021183A1 (de)	1996-11-11	1997-11-11	Enantiomerenreine, basische aryl-cycloalkyl-hydroxycarbonsäureester, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln

Publications (3)

Publication Number	Publication Date
NO991056D0 NO991056D0 (no)	1999-03-03
NO991056L NO991056L (no)	1999-05-11
NO314354B1 true NO314354B1 (no)	2003-03-10

Family

ID=3525062

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19991056A NO314354B1 (no)	1996-11-11	1999-03-03	Enantiomerrene estere, fremgangsmåte for deres fremstilling og deres anvendelse i legemidler

Country Status (18)

Country	Link
US (1)	US6307060B1 (da)
EP (3)	EP1369414A1 (da)
JP (1)	JP2001504459A (da)
CN (1)	CN100391942C (da)
AT (1)	ATE238280T1 (da)
AU (1)	AU745331B2 (da)
CA (1)	CA2271276C (da)
DE (1)	DE59709927D1 (da)
DK (2)	DK0937041T3 (da)
ES (2)	ES2195121T3 (da)
HU (1)	HU228273B1 (da)
NO (1)	NO314354B1 (da)
NZ (1)	NZ336202A (da)
PL (1)	PL195520B1 (da)
PT (2)	PT937041E (da)
RU (1)	RU2238936C2 (da)
SI (2)	SI0937041T1 (da)
WO (1)	WO1998021183A1 (da)

Families Citing this family (40)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100391942C (zh) *	1996-11-11	2008-06-04	索佛特克两合公司	对映异构纯的碱性芳基-环烷基-羟基羧酸酯,其制备方法及其在药品中的应用
US6613795B2 (en)	1996-11-11	2003-09-02	Christian Noe	Enantiomerically pure basic arylcycloalkylhydroxycarboxylic esters, processes for their preparation and their use in medicaments
GB0008660D0 (en) *	2000-04-07	2000-05-31	Arakis Ltd	The treatment of respiratory diseases
EP1302458A4 (en)	2000-07-11	2005-10-19	Banyu Pharma Co Ltd	ESTERDERIVATE
ES2206021B1 (es) *	2002-04-16	2005-08-01	Almirall Prodesfarma, S.A.	Nuevos derivados de pirrolidinio.
AT412088B (de) *	2002-12-18	2004-09-27	Pharmacon Forschung & Beratung Gmbh	Verfahren zur herstellung der r,r oder s,s konfigurierten glycopyrronium-isomere
AU2002347552A1 (en)	2002-12-23	2004-07-14	Ranbaxy Laboratories Limited	1-substituted-3-pyrrolidine derivatives as muscarinic receptor antagonists
EA009059B1 (ru) *	2003-04-10	2007-10-26	Рэнбакси Лабораториз Лимитед	Замещенные производные азабициклогексана в качестве антагонистов мускаринового рецептора
PE20050231A1 (es)	2003-06-24	2005-05-20	Novartis Ag	Derivados de piperidinium y pirrolidinium como antagonistas del receptor muscarinico m3
ES2309705T3 (es)	2004-02-06	2008-12-16	MEDA PHARMA GMBH & CO. KG	Nueva combinacion de anticolinergico y beta-mimeticos para el tratamiento de enfermedades respiratorias.
GB0411056D0 (en)	2004-05-18	2004-06-23	Novartis Ag	Organic compounds
CA2568834A1 (en) *	2004-06-29	2006-01-12	Boehringer Ingelheim International Gmbh	Medicaments for inhalation comprising steroids and an anticholinergic
EP1616567A1 (en) *	2004-07-16	2006-01-18	Boehringer Ingelheim Pharma GmbH & Co.KG	Medicaments for inhalation comprising PDE IV inhibitors and glycopyrrolate salts
US20080262075A1 (en) *	2004-08-19	2008-10-23	Ranbaxy Laboratories Limited	Pyrrolidine Derivatives as Muscarinic Receptor Antagonists
GB0428418D0 (en)	2004-12-24	2005-02-02	Novartis Ag	Organic compounds
GB0428416D0 (en) *	2004-12-24	2005-02-02	Novartis Ag	Organic compounds
GB0504463D0 (en) *	2005-03-03	2005-04-13	Arakis Ltd	Method of crystallisation and purification
EP1863476B1 (en) *	2005-03-16	2016-02-03	MEDA Pharma GmbH & Co. KG	The combination of anticholinergics and leukotriene receptor antagonists for the treatment of respiratory diseases
TW200722418A (en) *	2005-04-20	2007-06-16	Astrazeneca Ab	Novel compounds
JP2008538758A (ja) *	2005-04-23	2008-11-06	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	抗コリン作用薬に加えてベータ受容体刺激薬及びステロイドを含有する吸入用の医薬組成物
NZ591969A (en) *	2005-12-21	2012-05-25	Meda Pharma Gmbh & Co Kg	Combination of anticholinergics, glucocorticoids, beta2-adrenoceptor agonists, PDE 4 inhibitor and antileukotriene for the treatment of inflammatory diseases
GB0613161D0 (en)	2006-06-30	2006-08-09	Novartis Ag	Organic Compounds
TW200825084A (en)	2006-11-14	2008-06-16	Astrazeneca Ab	New compounds 521
EA017627B1 (ru)	2008-05-13	2013-01-30	Астразенека Аб	Хинуклидиновые производные в качестве антагонистов мускаринового м3 рецептора
PL3111927T3 (pl) *	2009-05-29	2020-06-29	Pearl Therapeutics, Inc.	Kompozycje do wziewnego podawania środków aktywnych oraz związane z nimi sposoby i systemy
WO2011094434A2 (en) *	2010-01-28	2011-08-04	Theron Pharmaceuticals, Inc.	7-azoniabicyclo [2.2.1] heptane derivatives, methods of production, and pharmaceutical uses thereof
RU2569852C2 (ru) *	2010-06-14	2015-11-27	КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А.	Кристаллическая форма гликопиррония хлорида
EP2580194A1 (en) *	2010-06-14	2013-04-17	Chiesi Farmaceutici S.p.A.	Process for the preparation of glycopyrronium chloride
JOP20120023B1 (ar)	2011-02-04	2022-03-14	Novartis Ag	صياغات مساحيق جافة من جسيمات تحتوي على واحد أو اثنين من المواد الفعالة لعلاج امراض ممرات الهواء الانسدادية او الالتهابية
CN102627595A (zh) *	2012-03-09	2012-08-08	徐奎	一种制备格隆溴铵的方法
US8558008B2 (en)	2013-02-28	2013-10-15	Dermira, Inc.	Crystalline glycopyrrolate tosylate
US9006462B2 (en)	2013-02-28	2015-04-14	Dermira, Inc.	Glycopyrrolate salts
JP6114841B2 (ja)	2013-02-28	2017-04-12	ダーミラ，インク．Ｄｅｒｍｉｒａ，Ｉｎｃ．	グリコピロレート塩
AU2014229361B2 (en)	2013-03-14	2016-08-04	Novartis Ag	Deamorphization of spray-dried formulations via spray-blending
US9452139B2 (en)	2013-03-14	2016-09-27	Novartis Ag	Respirable agglomerates of porous carrier particles and micronized drug
CN104586841A (zh) *	2013-10-30	2015-05-06	中国药科大学	(3r,2’r)-格隆溴铵作为m3毒蕈碱性受体拮抗剂在制药中的用途
US9926270B2 (en)	2014-08-20	2018-03-27	Dermira, Inc.	Process for production of glycopyrronium tosylate
EP3237378B1 (en) *	2014-12-24	2018-09-26	Laboratorios Lesvi, S.L.	Process for preparing (3rs)-3-[(2sr)-(2-cyclopentyl-2-hydroxy-2-phenylacetyl)oxy]-1,1-dimethylpyrrolidinium bromide
CN107304178B (zh) *	2016-04-21	2020-03-27	辽宁药联制药有限公司	一种毒蕈碱受体拮抗剂格隆溴铵手性对映体的制备方法
WO2018026869A1 (en)	2016-08-02	2018-02-08	Dermira, Inc.	Processes for making, and methods of using, glycopyrronium compounds

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2882276A (en) *		1959-04-14		Certain esters of amino alcohols
US3157671A (en) *		1964-11-17		Ljl-diethyl-a-hydroxypyrrolidimum
US2980693A (en) *		1961-04-18		Methods for producing same
CA625276A (en) *		1961-08-08	D. Lunsford Carl	Esters of amino alcohols
CA629039A (en) *		1961-10-10	A.H. Robins Company	1-substituted-3-pyrrolidyl benzilates
GB821436A (en) *	1956-02-22	1959-10-07	Parke Davis & Co	3-pyrrolidinyl benzilates
CH375358A (de) *	1957-06-17	1964-02-29	Robins Co Inc A H	Verfahren zur Herstellung von Estern von N-substituierten 3-Pyrrolidinolen
US2958028A (en) *	1957-11-01	1960-10-25	Collins Radio Co	Remote control system
US2956062A (en) *	1959-02-26	1960-10-11	Robins Co Inc A H	Esters of amino alcohols
US3185702A (en) *	1959-03-16	1965-05-25	Lunsford Carl Dalton	Basic esters of 3-aryl-3-pyrrolidinols
GB885430A (en) *	1960-08-17	1961-12-28	Loewe Opta Ag	Arrangement for receiving stereophonic transmissions
GB1170831A (en) *	1967-02-01	1969-11-19	Robins Co Inc A H	O-Substituted Pyrrolidinols and S-Substituted Thiopyrrolidinols and Processes for their Preparation
US3691198A (en) *	1970-12-21	1972-09-12	Cpc International Inc	Synthesis of 1-substituted-3-halopyrrolidines
FI49713C (fi) *	1974-05-15	1975-09-10	Medica Pharma Co Ltd	Terapeuttisesti tehokkaan erytro-1-metyyli-3-pyrrolidinyyli-alfa-syklo -pentyylimandelaattimetobromidin valmistusmenetelmä.
US4208423A (en) *	1978-11-24	1980-06-17	Syntex Inc.	Anticholinergic bronchodilators
US4228171A (en) *	1979-03-05	1980-10-14	Syntex (U.S.A.) Inc.	Antichlorinergic bronchodilators
SU1416056A3 (ru) *	1983-01-21	1988-08-07	Алкалоида Ведьесети Дьяр (Инопредприятие)	Способ получени производных пирролидина или их солей с неорганической кислотой
US4721722A (en) *	1985-07-12	1988-01-26	United Pharmaceuticals, Inc.	Anti-spasmodic agents containing quaternary nitrogen
US5750540A (en) *	1995-04-28	1998-05-12	Banyu Pharmaceutical Co., Ltd.	1,4-di-substituted piperidine derivatives
EP0909172A4 (en)	1996-07-01	1999-06-09	Sepracor Inc	METHODS AND COMPOSITIONS FOR TREATING URINARY INCONTINENCE WITH ENANTIOMERIC ENRICHED (R, s) -GLYCOPYRROLATE
US6063808A (en)	1996-07-01	2000-05-16	Sepracor Inc.	Methods and compositions for treating urinary incontinence using enantiomerically enriched (S,S)-glycopyrrolate
CN100391942C (zh) *	1996-11-11	2008-06-04	索佛特克两合公司	对映异构纯的碱性芳基-环烷基-羟基羧酸酯,其制备方法及其在药品中的应用
US6603808B1 (en)	1999-07-22	2003-08-05	Compaq Information Technologies Group, L.P.	Dual mode phone line networking modem utilizing conventional telephone wiring

1997
- 1997-11-11 CN CNB971996210A patent/CN100391942C/zh not_active Expired - Fee Related
- 1997-11-11 AU AU48560/97A patent/AU745331B2/en not_active Ceased
- 1997-11-11 NZ NZ336202A patent/NZ336202A/xx not_active IP Right Cessation
- 1997-11-11 EP EP03005233A patent/EP1369414A1/de not_active Withdrawn
- 1997-11-11 WO PCT/AT1997/000245 patent/WO1998021183A1/de not_active Ceased
- 1997-11-11 EP EP03005232A patent/EP1371645B1/de not_active Expired - Lifetime
- 1997-11-11 PL PL97332595A patent/PL195520B1/pl unknown
- 1997-11-11 DE DE59709927T patent/DE59709927D1/de not_active Expired - Lifetime
- 1997-11-11 PT PT97911049T patent/PT937041E/pt unknown
- 1997-11-11 EP EP97911049A patent/EP0937041B1/de not_active Expired - Lifetime
- 1997-11-11 RU RU99112115/04A patent/RU2238936C2/ru not_active IP Right Cessation
- 1997-11-11 HU HU9903791A patent/HU228273B1/hu not_active IP Right Cessation
- 1997-11-11 PT PT3005232T patent/PT1371645E/pt unknown
- 1997-11-11 CA CA002271276A patent/CA2271276C/en not_active Expired - Fee Related
- 1997-11-11 JP JP52194298A patent/JP2001504459A/ja active Pending
- 1997-11-11 ES ES97911049T patent/ES2195121T3/es not_active Expired - Lifetime
- 1997-11-11 AT AT97911049T patent/ATE238280T1/de active
- 1997-11-11 DK DK97911049T patent/DK0937041T3/da active
- 1997-11-11 SI SI9730556T patent/SI0937041T1/xx unknown
- 1997-11-11 SI SI9730800T patent/SI1371645T1/sl unknown
- 1997-11-11 ES ES03005232T patent/ES2407135T3/es not_active Expired - Lifetime
- 1997-11-11 DK DK03005232.8T patent/DK1371645T3/da active
1999
- 1999-03-03 NO NO19991056A patent/NO314354B1/no not_active IP Right Cessation
- 1999-05-11 US US09/309,960 patent/US6307060B1/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
RU2238936C2 (ru)	2004-10-27
US6307060B1 (en)	2001-10-23
NZ336202A (en)	2000-10-27
PT937041E (pt)	2003-09-30
CA2271276C (en)	2009-01-13
HU228273B1 (en)	2013-02-28
EP1369414A1 (de)	2003-12-10
ES2195121T3 (es)	2003-12-01
ATE238280T1 (de)	2003-05-15
DK1371645T3 (da)	2013-06-03
DE59709927D1 (de)	2003-05-28
SI1371645T1 (sl)	2013-07-31
PL195520B1 (pl)	2007-09-28
PT1371645E (pt)	2013-05-21
EP1371645B1 (de)	2013-02-20
CA2271276A1 (en)	1998-05-22
EP1371645A1 (de)	2003-12-17
EP0937041A1 (de)	1999-08-25
CN1237159A (zh)	1999-12-01
HUP9903791A2 (hu)	2000-03-28
SI0937041T1 (en)	2003-10-31
AU745331B2 (en)	2002-03-21
DK0937041T3 (da)	2003-08-11
JP2001504459A (ja)	2001-04-03
HUP9903791A3 (en)	2001-10-29
NO991056L (no)	1999-05-11
HK1061023A1 (en)	2004-09-03
NO991056D0 (no)	1999-03-03
AU4856097A (en)	1998-06-03
ES2407135T3 (es)	2013-06-11
EP0937041B1 (de)	2003-04-23
CN100391942C (zh)	2008-06-04
WO1998021183A1 (de)	1998-05-22
PL332595A1 (en)	1999-09-27

Legal Events

Date	Code	Title	Description
2017-06-26	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO314354B1 (no)	2003-03-10	Enantiomerrene estere, fremgangsmåte for deres fremstilling og deres anvendelse i legemidler
US7253182B2 (en)	2007-08-07	Enantiomerically pure basic arylcycloalkylhydroxycarboxylic esters, processes for their preparation and their use in medicaments
IL174942A (en)	2011-03-31	Derivatives of n-[phenyl(piperidine-2-yl)methyl]arylamides, pharmaceutical compositions comprising them and their use in the preparation of medicaments
JP6030120B2 (ja)	2016-11-24	Ｃｎｓ障害の治療におけるジベンゾチアゼピン誘導体およびその使用
JPH08505375A (ja)	1996-06-11	置換基をもつトリオール類
US20030166629A1 (en)	2003-09-04	Cyclic quaternary ammonium compounds
KR20130098174A (ko)	2013-09-04	글리코피로니움 클로라이드의 제조 방법
JP2010504311A (ja)	2010-02-12	ピロリジン、インドリジンおよびキノリジンの誘導体、これらの調製およびこれらの治療上の使用
ITMI951930A1 (it)	1997-03-15	Derivati di diarilalchenilammina
WO1995000486A1 (en)	1995-01-05	N-substituted azaheterocyclic carboxylic acids and esters thereof
MX2015001769A (es)	2015-05-08	Sales cuaternarias de piperidinio.
CN117362200B (zh)	2024-04-09	苯甲胺类化合物及其合成方法与应用
CH695982A5 (de)	2006-11-15	Inhibitor der Monaminaufnahme.
KR930000113B1 (ko)	1993-01-09	아조니아스피로노르트로판올 에스테르의 제조방법
US5508401A (en)	1996-04-16	Substituted dibenzo[a,d]cycloheptene NMDA antagonists
AU695312B2 (en)	1998-08-13	Alpha-(4-chlorophenyl)-4-{(4-fluorophenyl)-methyl}piperidine -1-ethanol esters, their preparation and their therapeutic application
AU2023365108A1 (en)	2025-05-01	Preparation of phenethylamines and cathinones and stereoisomers thereof and precursors thereof
JP2025527600A (ja)	2025-08-22	グルコシルセラミド合成酵素阻害薬の結晶形及びその使用
HK40122714A (zh)	2025-10-03	作为血清素能剂用於治疗相关障碍的吲哚啉衍生物
HK40105243A (zh)	2024-08-09	作为血清素能药物的用於治疗与之相关的疾病的吲哚衍生物
JPWO2001007406A1 (ja)	2003-02-12	新規アミド誘導体
HK1061022A (en)	2004-09-03	Enantiomerically pure arylcycloalkyl hydroxycarboxylic esters, processes for their preparation and their use as modulators of muscarinic receptors