JPH043378B2 - - Google Patents
Info
- Publication number
- JPH043378B2 JPH043378B2 JP59146553A JP14655384A JPH043378B2 JP H043378 B2 JPH043378 B2 JP H043378B2 JP 59146553 A JP59146553 A JP 59146553A JP 14655384 A JP14655384 A JP 14655384A JP H043378 B2 JPH043378 B2 JP H043378B2
- Authority
- JP
- Japan
- Prior art keywords
- salt
- aminobutyric acid
- dihydroxy
- methylpentyramide
- effect
- 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
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 27
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 23
- OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 claims description 12
- 229960003692 gamma aminobutyric acid Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 5
- 159000000007 calcium salts Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000000694 effects Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 11
- 239000003814 drug Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- JYVXNLLUYHCIIH-LURJTMIESA-N mevalonolactone Chemical compound C[C@]1(O)CCOC(=O)C1 JYVXNLLUYHCIIH-LURJTMIESA-N 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000011575 calcium Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 210000004556 brain Anatomy 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 230000006742 locomotor activity Effects 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229960001252 methamphetamine Drugs 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229930003347 Atropine Natural products 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 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 3
- 229960000396 atropine Drugs 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 230000035863 hyperlocomotion Effects 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 229960001412 pentobarbital Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000004622 sleep time Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229940124277 aminobutyric acid Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- SBBDHANTMHIRGW-QMMMGPOBSA-N hopantenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCC(O)=O SBBDHANTMHIRGW-QMMMGPOBSA-N 0.000 description 2
- 229950001260 hopantenic acid Drugs 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- -1 isonicotinoyl γ-aminobutyric acid Chemical compound 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000037081 physical activity Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KJTLQQUUPVSXIM-ZCFIWIBFSA-N (R)-mevalonic acid Chemical compound OCC[C@](O)(C)CC(O)=O KJTLQQUUPVSXIM-ZCFIWIBFSA-N 0.000 description 1
- NHNHLPJQBDXKSO-UHFFFAOYSA-N 4-amino-2-(pyridine-3-carbonyl)butanoic acid Chemical compound NCCC(C(O)=O)C(=O)C1=CC=CN=C1 NHNHLPJQBDXKSO-UHFFFAOYSA-N 0.000 description 1
- KJTLQQUUPVSXIM-UHFFFAOYSA-N DL-mevalonic acid Natural products OCCC(O)(C)CC(O)=O KJTLQQUUPVSXIM-UHFFFAOYSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010047513 Vision blurred Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000008499 blood brain barrier function Effects 0.000 description 1
- 210000001218 blood-brain barrier Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- 150000004652 butanoic acids Chemical class 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000517 effect on sleep Effects 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000004623 sleep-prolonging effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14655384A JPS6124552A (ja) | 1984-07-13 | 1984-07-13 | γ−アミノ酪酸誘導体およびその製造法 |
| US06/753,613 US4703061A (en) | 1984-07-13 | 1985-07-09 | Gamma-aminobutyric acid derivatives, process for production thereof, and use thereof as medicaments |
| DE8585108744T DE3564680D1 (en) | 1984-07-13 | 1985-07-12 | Gamma-aminobutyric acid derivatives, process for production thereof, and use thereof as medicaments |
| EP85108744A EP0170933B1 (en) | 1984-07-13 | 1985-07-12 | Gamma-aminobutyric acid derivatives, process for production thereof, and use thereof as medicaments |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14655384A JPS6124552A (ja) | 1984-07-13 | 1984-07-13 | γ−アミノ酪酸誘導体およびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6124552A JPS6124552A (ja) | 1986-02-03 |
| JPH043378B2 true JPH043378B2 (enEXAMPLES) | 1992-01-23 |
Family
ID=15410263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14655384A Granted JPS6124552A (ja) | 1984-07-13 | 1984-07-13 | γ−アミノ酪酸誘導体およびその製造法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4703061A (enEXAMPLES) |
| EP (1) | EP0170933B1 (enEXAMPLES) |
| JP (1) | JPS6124552A (enEXAMPLES) |
| DE (1) | DE3564680D1 (enEXAMPLES) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2045515C1 (ru) * | 1993-06-30 | 1995-10-10 | Научно-производственное объединение "Витамины" | Кетопантоиламинобутират кальция, обладающий седативным действием |
| US6306909B1 (en) | 1997-03-12 | 2001-10-23 | Queen's University At Kingston | Anti-epileptogenic agents |
| JP2004538258A (ja) * | 2001-03-13 | 2004-12-24 | クイーンズ ユニバーシティ アット キングストン | 抗癲癇誘発剤 |
| WO2002096424A1 (en) * | 2001-05-25 | 2002-12-05 | Queen's University At Kingston | Hetereocyclic beta-aminoacids and their use as anti-epileptogenic agents |
| CN102356037A (zh) * | 2009-03-17 | 2012-02-15 | 三菱电机株式会社 | 电梯的夹紧装置及电梯的支承装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2271872A (en) * | 1940-03-25 | 1942-02-03 | Research Corp | Production of growth promoting substances |
| US2414682A (en) * | 1940-04-08 | 1947-01-21 | Research Corp | Production of pantothenic acid and other related growth promoting substances |
| US2234680A (en) * | 1940-07-22 | 1941-03-11 | Abbott Lab | Process of preparing pantothenic acid |
| GB553317A (en) * | 1941-02-26 | 1943-05-17 | Merck & Co Inc | Improvements in the production of alkaline earth metal pantothenates |
| US2442143A (en) * | 1941-06-06 | 1948-05-25 | Nopco Chem Co | Synthesis of pantothenic acid and its salts |
| GB561877A (en) * | 1942-01-17 | 1944-06-08 | Lederle Lab Inc | Improvements in or relating to calcium pantothenate and methods of preparing same |
| US2848489A (en) * | 1954-12-17 | 1958-08-19 | Upjohn Co | Preparation of alkaline-earth salts of pantothenic acid |
| US2856421A (en) * | 1955-09-06 | 1958-10-14 | Abbott Lab | Crystalline salts of pantothenic acid |
| JPS5517329A (en) * | 1978-07-21 | 1980-02-06 | Tanabe Seiyaku Co Ltd | Remedy for dementia and dotage |
-
1984
- 1984-07-13 JP JP14655384A patent/JPS6124552A/ja active Granted
-
1985
- 1985-07-09 US US06/753,613 patent/US4703061A/en not_active Expired - Fee Related
- 1985-07-12 EP EP85108744A patent/EP0170933B1/en not_active Expired
- 1985-07-12 DE DE8585108744T patent/DE3564680D1/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| EP0170933A1 (en) | 1986-02-12 |
| JPS6124552A (ja) | 1986-02-03 |
| US4703061A (en) | 1987-10-27 |
| DE3564680D1 (en) | 1988-10-06 |
| EP0170933B1 (en) | 1988-08-31 |
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