DE2937489C2 - - Google Patents
Info
- Publication number
- DE2937489C2 DE2937489C2 DE2937489A DE2937489A DE2937489C2 DE 2937489 C2 DE2937489 C2 DE 2937489C2 DE 2937489 A DE2937489 A DE 2937489A DE 2937489 A DE2937489 A DE 2937489A DE 2937489 C2 DE2937489 C2 DE 2937489C2
- Authority
- DE
- Germany
- Prior art keywords
- bladder
- compound
- effect
- atropine
- side effects
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 22
- 230000000694 effects Effects 0.000 description 20
- 239000003814 drug Substances 0.000 description 14
- 229940079593 drug Drugs 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 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 10
- 229930003347 Atropine Natural products 0.000 description 9
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 9
- 229960000396 atropine Drugs 0.000 description 9
- 230000002048 spasmolytic effect Effects 0.000 description 7
- 239000000812 cholinergic antagonist Substances 0.000 description 6
- 230000003153 cholinolytic effect Effects 0.000 description 6
- 238000002560 therapeutic procedure Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 230000001225 therapeutic effect Effects 0.000 description 5
- PYHXGXCGESYPCW-UHFFFAOYSA-N diphenylacetic acid Chemical class C=1C=CC=CC=1C(C(=O)O)C1=CC=CC=C1 PYHXGXCGESYPCW-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 231100000027 toxicology Toxicity 0.000 description 4
- 206010036018 Pollakiuria Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical class C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 210000003405 ileum Anatomy 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 230000007774 longterm Effects 0.000 description 3
- 239000000902 placebo Substances 0.000 description 3
- 229940068196 placebo Drugs 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- UVKFSMBPRQBNCH-UHFFFAOYSA-M 4,4-diphenylbutan-2-yl-ethyl-dimethylazanium;bromide Chemical compound [Br-].C=1C=CC=CC=1C(CC(C)[N+](C)(C)CC)C1=CC=CC=C1 UVKFSMBPRQBNCH-UHFFFAOYSA-M 0.000 description 2
- 208000028048 Accommodation disease Diseases 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- 208000008967 Enuresis Diseases 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 238000004820 blood count Methods 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 206010013781 dry mouth Diseases 0.000 description 2
- 229960002493 emepronium bromide Drugs 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 238000012153 long-term therapy Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- -1 methylpiperidyl Chemical group 0.000 description 2
- 230000027939 micturition Effects 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 206010029446 nocturia Diseases 0.000 description 2
- 230000002040 relaxant effect Effects 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 230000002485 urinary effect Effects 0.000 description 2
- NCBHOFSYIAZVJH-UHFFFAOYSA-N 1-methylpiperidin-2-ol Chemical compound CN1CCCCC1O NCBHOFSYIAZVJH-UHFFFAOYSA-N 0.000 description 1
- 238000012935 Averaging Methods 0.000 description 1
- 206010005063 Bladder pain Diseases 0.000 description 1
- 206010048994 Bladder spasm Diseases 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 208000004547 Hallucinations Diseases 0.000 description 1
- ZTVIKZXZYLEVOL-MCOXGKPRSA-N Homatropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-MCOXGKPRSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- GZHFODJQISUKAY-UHFFFAOYSA-N Methantheline Chemical compound C1=CC=C2C(C(=O)OCC[N+](C)(CC)CC)C3=CC=CC=C3OC2=C1 GZHFODJQISUKAY-UHFFFAOYSA-N 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 208000006550 Mydriasis Diseases 0.000 description 1
- VVWYOYDLCMFIEM-UHFFFAOYSA-N Propantheline Chemical compound C1=CC=C2C(C(=O)OCC[N+](C)(C(C)C)C(C)C)C3=CC=CC=C3OC2=C1 VVWYOYDLCMFIEM-UHFFFAOYSA-N 0.000 description 1
- 206010057071 Rectal tenesmus Diseases 0.000 description 1
- 208000000921 Urge Urinary Incontinence Diseases 0.000 description 1
- 208000012931 Urologic disease Diseases 0.000 description 1
- PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- YBCNXCRZPWQOBR-WVHCHWADSA-N butylscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 YBCNXCRZPWQOBR-WVHCHWADSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000035558 fertility Effects 0.000 description 1
- 230000001558 histaminolytic effect Effects 0.000 description 1
- 229960000857 homatropine Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229960001470 methantheline Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- LZCOQTDXKCNBEE-IKIFYQGPSA-N methscopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)C)=CC=CC=C1 LZCOQTDXKCNBEE-IKIFYQGPSA-N 0.000 description 1
- 229960001383 methylscopolamine Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 230000000422 nocturnal effect Effects 0.000 description 1
- 208000005346 nocturnal enuresis Diseases 0.000 description 1
- 229940053544 other antidepressants in atc Drugs 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 229960000697 propantheline Drugs 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000003236 psychic effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 229950009846 scopolamine butylbromide Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 208000012271 tenesmus Diseases 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 206010046494 urge incontinence Diseases 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD78208336A DD139212A1 (de) | 1978-10-09 | 1978-10-09 | Verfahren zur herstellung eines neuen arzneimittels aus alpha,alpha-diphenyl-alpha-alkoxyessigsaeure-1-methylpiperidyl-4-ester-derivaten |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2937489A1 DE2937489A1 (de) | 1980-04-17 |
DE2937489C2 true DE2937489C2 (enrdf_load_stackoverflow) | 1990-08-02 |
Family
ID=5514770
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19792937489 Granted DE2937489A1 (de) | 1978-10-09 | 1979-09-17 | Arzneimittel zur behandlung hypertoner funktionszustaende der harnblase |
Country Status (5)
Country | Link |
---|---|
JP (1) | JPS5555117A (enrdf_load_stackoverflow) |
CH (1) | CH644016A5 (enrdf_load_stackoverflow) |
DD (1) | DD139212A1 (enrdf_load_stackoverflow) |
DE (1) | DE2937489A1 (enrdf_load_stackoverflow) |
GB (1) | GB2031727B (enrdf_load_stackoverflow) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10129832A1 (de) * | 2001-06-17 | 2003-07-10 | Berolina Drug Dev Ab Svedala | Deuterierte N- und alpha-substituierte Diphenylalkoxyessigsäureaminoalkylester sowie diese Verbindungen enthaltende Arzneimittel |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3742580C1 (de) * | 1987-12-16 | 1989-05-11 | Schaper & Bruemmer Gmbh | Verwendung des alpha,alpha-Diphenyl-alpha-(3-carboxy-propionyloxy)-essigsaeure-4-(N-methylpiperidyl)-esters zur Behandlung hypertoner Funktionszustaende im Bereich der Harnblase |
DE10149674A1 (de) | 2001-10-09 | 2003-04-24 | Apogepha Arzneimittel Gmbh | Orale Darreichungsformen für Propiverin oder seinen pharmazeutisch annehmbaren Salzen mit verlängerter Wirkstoffreisetzung |
US7851633B2 (en) | 2006-06-09 | 2010-12-14 | Beiersdorf Ag | Piperidinium compounds and cosmetic compositions containing them |
CA2862990C (en) * | 2012-01-30 | 2017-10-24 | Taiho Pharmaceutical Co., Ltd. | Novel acetic acid ester compound or salt thereof |
ES2612827T3 (es) | 2012-05-15 | 2017-05-18 | Taiho Pharmaceutical Co., Ltd. | Agente profiláctico y/o agente terapéutico para incontinencia urinaria de esfuerzo |
AU2014271739B2 (en) * | 2013-05-30 | 2016-07-28 | Taiho Pharmaceutical Co., Ltd. | Novel fluorinated benzilic acid ester compound, and salt thereof |
-
1978
- 1978-10-09 DD DD78208336A patent/DD139212A1/xx unknown
-
1979
- 1979-09-17 DE DE19792937489 patent/DE2937489A1/de active Granted
- 1979-09-28 GB GB7933790A patent/GB2031727B/en not_active Expired
- 1979-10-05 CH CH900479A patent/CH644016A5/de not_active IP Right Cessation
- 1979-10-06 JP JP12934579A patent/JPS5555117A/ja active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10129832A1 (de) * | 2001-06-17 | 2003-07-10 | Berolina Drug Dev Ab Svedala | Deuterierte N- und alpha-substituierte Diphenylalkoxyessigsäureaminoalkylester sowie diese Verbindungen enthaltende Arzneimittel |
Also Published As
Publication number | Publication date |
---|---|
DD139212A1 (de) | 1979-12-19 |
DE2937489A1 (de) | 1980-04-17 |
GB2031727A (en) | 1980-04-30 |
JPS6251242B2 (enrdf_load_stackoverflow) | 1987-10-29 |
CH644016A5 (de) | 1984-07-13 |
JPS5555117A (en) | 1980-04-22 |
GB2031727B (en) | 1982-11-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8127 | New person/name/address of the applicant |
Owner name: VEB SAECHSISCHES SERUMWERK DRESDEN, DDR 8012 DRESD |
|
8110 | Request for examination paragraph 44 | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8327 | Change in the person/name/address of the patent owner |
Owner name: APOGEPHA ARZNEIMITTEL GMBH, O-8019 DRESDEN, DE |
|
8381 | Inventor (new situation) |
Free format text: SCHUBERT, GEB. RICHTER, GERTRUD, DIPL.-BIOL. DR.RER.NAT., O-8051 DRESDEN, DE STARKE, CHRISTIAN, DIPL.-CHEM., O-8053 DRESDEN, DE PEIN, ECKHARDT, DR., 3410 NORTHEIM, DE |
|
V448 | Application of spc |
Free format text: PRODUCT NAME: PROPIVERINHYDROCHLORID; REGISTRATION NO/DATE: NICHT BEKANNT, 19981021 Spc suppl protection certif: 198 75 042 Filing date: 19981021 |
|
V448 | Application of spc |
Free format text: PRODUCT NAME: PROPIVERINHYDROCHLORID; REGISTRATION NO/DATE: 44279.00.00, 19981221 Spc suppl protection certif: 199 75 038 Filing date: 19990515 |
|
V457 | Spc granted |
Free format text: PRODUCT NAME: PROPIVERINHYDROCHLORID; REGISTRATION NO/DATE: 44279.00.00, 19981221 Spc suppl protection certif: 199 75 038 Filing date: 19990515 |
|
V454 | Spc application withdrawn or to be regarded as withdrawn |
Free format text: PRODUCT NAME: PROPIVERINHYDROCHLORID; REGISTRATION NO/DATE: NICHT BEKANNT, 19981021 Spc suppl protection certif: 198 75 042 Filing date: 19981021 |
|
V464 | Spc expired |
Free format text: PRODUCT NAME: PROPIVERINHYDROCHLORID; REGISTRATION NO/DATE: 44279.00.00, 19981221 Spc suppl protection certif: 199 75 038 Filing date: 19990515 |