HU204047B - Process for producing pilocarpine derivatives and pharmaceutical compositions comprising such compounds - Google Patents
Process for producing pilocarpine derivatives and pharmaceutical compositions comprising such compounds Download PDFInfo
- Publication number
- HU204047B HU204047B HU88177A HU17788A HU204047B HU 204047 B HU204047 B HU 204047B HU 88177 A HU88177 A HU 88177A HU 17788 A HU17788 A HU 17788A HU 204047 B HU204047 B HU 204047B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- compound
- compounds
- alkyl
- preparation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 67
- 238000000034 method Methods 0.000 title claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 3
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical class C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 20
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- -1 carbamoyloxy Chemical group 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 230000001713 cholinergic effect Effects 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 3
- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 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 claims 1
- 206010039966 Senile dementia Diseases 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960001416 pilocarpine Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-M oxalate(1-) Chemical compound OC(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-M 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000003518 presynaptic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JBGWMRAMUROVND-UHFFFAOYSA-N 1-sulfanylidenethiophene Chemical compound S=S1C=CC=C1 JBGWMRAMUROVND-UHFFFAOYSA-N 0.000 description 1
- KNENSDLFTGIERH-UHFFFAOYSA-N 2,2,4,4-tetramethyl-3-phenylpentan-3-ol Chemical compound CC(C)(C)C(O)(C(C)(C)C)C1=CC=CC=C1 KNENSDLFTGIERH-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 206010000234 Abortion spontaneous Diseases 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 206010049119 Emotional distress Diseases 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 206010026749 Mania Diseases 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- RDYMFSUJUZBWLH-UHFFFAOYSA-N endosulfan Chemical compound C12COS(=O)OCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl RDYMFSUJUZBWLH-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 208000015994 miscarriage Diseases 0.000 description 1
- 239000000472 muscarinic agonist Substances 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 210000001640 nerve ending Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- RNAICSBVACLLGM-GNAZCLTHSA-N pilocarpine hydrochloride Chemical compound Cl.C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C RNAICSBVACLLGM-GNAZCLTHSA-N 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012262 resinous product Substances 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000000995 spontaneous abortion Diseases 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3702940 | 1987-01-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT50168A HUT50168A (en) | 1989-12-28 |
| HU204047B true HU204047B (en) | 1991-11-28 |
Family
ID=6319976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU88177A HU204047B (en) | 1987-01-31 | 1988-01-18 | Process for producing pilocarpine derivatives and pharmaceutical compositions comprising such compounds |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4835174A (enExample) |
| JP (1) | JPS63201185A (enExample) |
| KR (1) | KR880009013A (enExample) |
| AT (1) | AT395852B (enExample) |
| AU (1) | AU607966B2 (enExample) |
| BE (1) | BE1001005A3 (enExample) |
| CA (1) | CA1327805C (enExample) |
| CH (1) | CH675721A5 (enExample) |
| CS (1) | CS411291A3 (enExample) |
| DK (1) | DK46288A (enExample) |
| ES (1) | ES2008421A6 (enExample) |
| FI (1) | FI90080C (enExample) |
| FR (1) | FR2610322B1 (enExample) |
| GB (1) | GB2200910B (enExample) |
| GR (1) | GR880100042A (enExample) |
| HU (1) | HU204047B (enExample) |
| IE (1) | IE61989B1 (enExample) |
| IL (1) | IL85252A (enExample) |
| IT (1) | IT1219827B (enExample) |
| LU (1) | LU87122A1 (enExample) |
| MY (1) | MY102415A (enExample) |
| NL (1) | NL8800099A (enExample) |
| NZ (1) | NZ223359A (enExample) |
| PH (1) | PH24837A (enExample) |
| PT (1) | PT86666B (enExample) |
| SE (1) | SE466150B (enExample) |
| ZA (1) | ZA88665B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4882343A (en) * | 1987-08-28 | 1989-11-21 | G. D. Searle & Co. | Biarylalkylimidazole derivatives as anti-depressants |
| US5861431A (en) * | 1995-06-07 | 1999-01-19 | Iotek, Inc. | Incontinence treatment |
| BR112020009361A2 (pt) | 2017-11-17 | 2020-10-13 | Cellix Bio Private Limited | composto de fórmula i, composição farmacêutica para tratar um distúrbio ocular ou complicações do mesmo, método de síntese de composto, método de tratamento de um distúrbio ocular ou complicações do mesmo em um indivíduo que precisa do mesmo e uso de um composto |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2457047A (en) * | 1946-02-13 | 1948-12-21 | Monsanto Chemicals | 2-(2'-thenyl)-4, 5-dihydroimidazoles and process for making the same |
| GB1601310A (en) * | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| JPS56131579A (en) * | 1980-03-17 | 1981-10-15 | Kissei Pharmaceut Co Ltd | Novel 1-substituted imidazole derivative |
| JPS58150566A (ja) * | 1982-03-03 | 1983-09-07 | Yoshitomi Pharmaceut Ind Ltd | 新規イミダゾ−ル誘導体 |
| DE3228266A1 (de) * | 1982-07-29 | 1984-02-02 | A. Nattermann & Cie GmbH, 5000 Köln | Imidazolylalkylthiophene, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| DE3329028A1 (de) * | 1983-08-11 | 1985-02-28 | Cassella Ag, 6000 Frankfurt | Substituierte (2-amino-2-imidazolin-1-yl)-essigsaeurederivate, verfahren zu ihrer herstellung, ihre verwendung und sie enthaltende pharmazeutische zubereitungen |
-
1988
- 1988-01-18 NL NL8800099A patent/NL8800099A/nl not_active Application Discontinuation
- 1988-01-18 HU HU88177A patent/HU204047B/hu not_active IP Right Cessation
- 1988-01-26 BE BE8800091A patent/BE1001005A3/fr not_active IP Right Cessation
- 1988-01-27 FR FR888801019A patent/FR2610322B1/fr not_active Expired - Lifetime
- 1988-01-27 GB GB8801804A patent/GB2200910B/en not_active Expired - Lifetime
- 1988-01-28 CH CH307/88A patent/CH675721A5/de not_active IP Right Cessation
- 1988-01-28 CA CA000557576A patent/CA1327805C/en not_active Expired - Fee Related
- 1988-01-28 LU LU87122A patent/LU87122A1/fr unknown
- 1988-01-29 IE IE24488A patent/IE61989B1/en not_active IP Right Cessation
- 1988-01-29 ES ES8800263A patent/ES2008421A6/es not_active Expired
- 1988-01-29 IT IT47578/88A patent/IT1219827B/it active
- 1988-01-29 MY MYPI88000081A patent/MY102415A/en unknown
- 1988-01-29 AT AT0018288A patent/AT395852B/de not_active IP Right Cessation
- 1988-01-29 DK DK046288A patent/DK46288A/da not_active Application Discontinuation
- 1988-01-29 GR GR880100042A patent/GR880100042A/el unknown
- 1988-01-29 AU AU10960/88A patent/AU607966B2/en not_active Ceased
- 1988-01-29 SE SE8800293A patent/SE466150B/sv not_active IP Right Cessation
- 1988-01-29 JP JP63021136A patent/JPS63201185A/ja active Pending
- 1988-01-29 ZA ZA88665A patent/ZA88665B/xx unknown
- 1988-01-29 FI FI880430A patent/FI90080C/fi not_active IP Right Cessation
- 1988-01-29 IL IL85252A patent/IL85252A/xx not_active IP Right Cessation
- 1988-01-29 PT PT86666A patent/PT86666B/pt not_active IP Right Cessation
- 1988-01-29 NZ NZ223359A patent/NZ223359A/en unknown
- 1988-01-29 PH PH36423A patent/PH24837A/en unknown
- 1988-01-29 US US07/149,812 patent/US4835174A/en not_active Expired - Fee Related
- 1988-01-30 KR KR1019880000895A patent/KR880009013A/ko not_active Ceased
-
1991
- 1991-12-27 CS CS914112A patent/CS411291A3/cs unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4147780A (en) | α-Amino-phosphonous acids for inhibiting bacteria and yeast | |
| HU202515B (en) | Process for producing new forscholine derivatives and pharmaceutical compositions comprising such compounds | |
| PL202463B1 (pl) | Pochodne galantaminy, sposób ich wytwarzania, środek leczniczy zawierajacy te pochodne, zastosowanie pochodnej galantaminy do wytwarzania środków leczniczych, sposób wytwarzania środków leczniczych oraz sposób oddzielania (+)- i (-)-izomerów | |
| DE69106902T2 (de) | Imidazopyridazine, ihre Herstellung und Verwendung. | |
| EP2880023A1 (fr) | Derives de griseofulvine | |
| JPH0261476B2 (enExample) | ||
| SK47894A3 (en) | 2-amino-4-chinolyl-dihydropyridines, method of their production treatments containing thereof, method of their production, and using of these compounds | |
| EP0440119A1 (en) | Imidazopyridazine compounds, their production and use | |
| HUT70488A (en) | Condensed quinolyl-dihydropyridine derivatives, pharmaceutical compositions containing them and process for producing the compounds and the pharmaceutical compositions | |
| DE69806189T2 (de) | Acronycinderivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zubereitungen | |
| FR2831884A1 (fr) | Nouveaux derives amides heteroaromatiques de 3 beta-amino azabicyclooctane, leur procede de preparation et leurs applications en therapeutique | |
| US4977176A (en) | Pilocarpine compounds which are used as pharmaceutical agents | |
| CA2119755A1 (fr) | Derives de benzonaphtyridine-1,8 et compositions antimicrobiennes | |
| EP1444234A2 (de) | Deuterierte pyrazolopyrimidinone sowie diese verbindungen enthaltende arzneimittel | |
| HU212268B (en) | Process to prepare phenyl-ethanol-amino- and phenyl-ethanol-amino-methyl-tetralin derivs. and pharmaceutical comns. contg. them as activ agent | |
| EP0827500B1 (en) | (2-morpholinylmethyl)benzamide derivatives | |
| US20030069417A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| DE60201264T2 (de) | Benzoaxathiepin-derivate und deren medizinische verwendung | |
| EP0003360B1 (de) | Neue Azathianaphthalinderivate, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate und ihre Verwendung | |
| US4835174A (en) | Pilocarpine derivatives | |
| DE69629703T2 (de) | Synthese von optisch reinen verbindungen als garft-inhibitoren und deren zwischenprodukte | |
| US4610986A (en) | Aminonaphthacene derivatives and their production | |
| MC2136A1 (fr) | Compose heterocycliques | |
| JPH05213962A (ja) | 三環チエノチオピラン類 | |
| US5508280A (en) | 5H-Dibenzo (A,D) cycloheptenes as muscarinic receptor antagonists |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |