DE2241241C3 - Thiazolo eckige klammer auf 3.2-a eckige klammer zu -pyrimidinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Thiazolo eckige klammer auf 3.2-a eckige klammer zu -pyrimidinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2241241C3 DE2241241C3 DE19722241241 DE2241241A DE2241241C3 DE 2241241 C3 DE2241241 C3 DE 2241241C3 DE 19722241241 DE19722241241 DE 19722241241 DE 2241241 A DE2241241 A DE 2241241A DE 2241241 C3 DE2241241 C3 DE 2241241C3
- Authority
- DE
- Germany
- Prior art keywords
- thiazolo
- angle
- acid
- ethanol
- production
- 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
Links
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 9
- 229940126601 medicinal product Drugs 0.000 title description 3
- CDUYCVWBLGEWSY-UHFFFAOYSA-N 5h-[1,3]thiazolo[3,2-a]pyrimidine Chemical compound C1C=CN=C2SC=CN12 CDUYCVWBLGEWSY-UHFFFAOYSA-N 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 16
- 238000002360 preparation method Methods 0.000 description 15
- 239000002253 acid Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 5
- 239000005751 Copper oxide Substances 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 229910000431 copper oxide Inorganic materials 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- -1 2-Phenyl-2,3-dihydro-5H-thiazolo [3,2-a] pyrimidin-5-one Chemical compound 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 3
- 235000011118 potassium hydroxide Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003518 caustics Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- LTMHNWPUDSTBKD-UHFFFAOYSA-N diethyl 2-(ethoxymethylidene)propanedioate Chemical compound CCOC=C(C(=O)OCC)C(=O)OCC LTMHNWPUDSTBKD-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229960005489 paracetamol Drugs 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- IZQLXJCCPVWMJV-UHFFFAOYSA-N 2h-1,3-benzothiazol-4-one Chemical compound O=C1C=CC=C2SCN=C12 IZQLXJCCPVWMJV-UHFFFAOYSA-N 0.000 description 1
- MBZLOOUKAILJOJ-UHFFFAOYSA-N 4-oxo-2,3a-dihydro-1,3-benzothiazole-3-carboxylic acid Chemical compound S1CN(C2C1=CC=CC2=O)C(=O)O MBZLOOUKAILJOJ-UHFFFAOYSA-N 0.000 description 1
- WZGXBOJKIJFMMC-UHFFFAOYSA-N 5-methyl-4,5-dihydro-1,3-thiazol-2-amine hydrobromide Chemical compound Br.CC1CN=C(N)S1 WZGXBOJKIJFMMC-UHFFFAOYSA-N 0.000 description 1
- PCIYONYENKIRKK-UHFFFAOYSA-N CC(C(C1=CC=CC=C1)SC1=NC=C2)N1C2=O Chemical compound CC(C(C1=CC=CC=C1)SC1=NC=C2)N1C2=O PCIYONYENKIRKK-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- NKLJEBMECDKNCM-UHFFFAOYSA-N OC(C1=NC=NCC1=O)=O Chemical compound OC(C1=NC=NCC1=O)=O NKLJEBMECDKNCM-UHFFFAOYSA-N 0.000 description 1
- FCLZCOCSZQNREK-UHFFFAOYSA-N Pyrrolidine, hydrochloride Chemical compound Cl.C1CCNC1 FCLZCOCSZQNREK-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3958571A GB1374281A (en) | 1971-08-24 | 1971-08-24 | Thiazolino-pyrimidin-5-one derivatives process for their pre paration and applications thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2241241A1 DE2241241A1 (de) | 1973-03-15 |
| DE2241241B2 DE2241241B2 (de) | 1977-06-02 |
| DE2241241C3 true DE2241241C3 (de) | 1978-01-19 |
Family
ID=10410359
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722241241 Expired DE2241241C3 (de) | 1971-08-24 | 1972-08-22 | Thiazolo eckige klammer auf 3.2-a eckige klammer zu -pyrimidinderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
| DE2264979A Expired DE2264979C3 (de) | 1971-08-24 | 1972-08-22 | Thiazolo[3,2-a]pyrimidin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2264979A Expired DE2264979C3 (de) | 1971-08-24 | 1972-08-22 | Thiazolo[3,2-a]pyrimidin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3876639A (enExample) |
| JP (1) | JPS5518718B2 (enExample) |
| AR (1) | AR204501A1 (enExample) |
| AT (1) | AT318626B (enExample) |
| BE (1) | BE787307A (enExample) |
| CA (1) | CA962677A (enExample) |
| CH (1) | CH540286A (enExample) |
| DE (2) | DE2241241C3 (enExample) |
| DK (1) | DK131470B (enExample) |
| ES (1) | ES406367A1 (enExample) |
| FR (1) | FR2150762B1 (enExample) |
| GB (1) | GB1374281A (enExample) |
| IE (1) | IE36874B1 (enExample) |
| IL (1) | IL40133A (enExample) |
| LU (1) | LU65936A1 (enExample) |
| NL (1) | NL149082B (enExample) |
| NO (1) | NO132761C (enExample) |
| OA (1) | OA04261A (enExample) |
| SE (1) | SE378599B (enExample) |
| ZA (1) | ZA725626B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4535081A (en) * | 1979-11-23 | 1985-08-13 | Pfizer Inc. | Antiallergic and antiulcer 1-oxo-1H-thiazolo[3,2-a]pyrimidine-2-carboxamides and intermediates therefor |
| US4443451A (en) * | 1981-07-15 | 1984-04-17 | Janssen Pharmaceutica N.V. | Bicyclic pyrimidin-5-one derivatives |
| US4562058A (en) * | 1983-08-02 | 1985-12-31 | International Minerals & Chemical Corp. | Process for crystallizing potassium sulfate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1209629A (en) * | 1966-11-29 | 1970-10-21 | Ciba Ltd | Novel pyrimido-benzthiazole and -benzoxazole compounds, process for their manufacture, and compositions containing them |
-
1971
- 1971-08-24 GB GB3958571A patent/GB1374281A/en not_active Expired
-
1972
- 1972-01-01 AR AR243711A patent/AR204501A1/es active
- 1972-08-07 CH CH1165672A patent/CH540286A/fr not_active IP Right Cessation
- 1972-08-08 BE BE787307A patent/BE787307A/xx unknown
- 1972-08-10 FR FR7228951A patent/FR2150762B1/fr not_active Expired
- 1972-08-14 US US280165A patent/US3876639A/en not_active Expired - Lifetime
- 1972-08-15 IL IL40133A patent/IL40133A/xx unknown
- 1972-08-15 IE IE1132/72A patent/IE36874B1/xx unknown
- 1972-08-16 ZA ZA725626A patent/ZA725626B/xx unknown
- 1972-08-21 JP JP8288772A patent/JPS5518718B2/ja not_active Expired
- 1972-08-21 DK DK413472AA patent/DK131470B/da unknown
- 1972-08-22 DE DE19722241241 patent/DE2241241C3/de not_active Expired
- 1972-08-22 CA CA149,965A patent/CA962677A/en not_active Expired
- 1972-08-22 LU LU65936A patent/LU65936A1/xx unknown
- 1972-08-22 DE DE2264979A patent/DE2264979C3/de not_active Expired
- 1972-08-22 NL NL727211463A patent/NL149082B/xx not_active IP Right Cessation
- 1972-08-23 SE SE7210922A patent/SE378599B/xx unknown
- 1972-08-23 AT AT728172A patent/AT318626B/de not_active IP Right Cessation
- 1972-08-23 ES ES406367A patent/ES406367A1/es not_active Expired
- 1972-08-23 NO NO3013/72A patent/NO132761C/no unknown
- 1972-08-23 OA OA54671A patent/OA04261A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1209629A (en) * | 1966-11-29 | 1970-10-21 | Ciba Ltd | Novel pyrimido-benzthiazole and -benzoxazole compounds, process for their manufacture, and compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| CH540286A (fr) | 1973-08-15 |
| LU65936A1 (enExample) | 1973-01-15 |
| GB1374281A (en) | 1974-11-20 |
| IL40133A0 (en) | 1972-10-29 |
| DE2241241B2 (de) | 1977-06-02 |
| OA04261A (fr) | 1979-12-31 |
| AR204501A1 (es) | 1976-02-12 |
| JPS5518718B2 (enExample) | 1980-05-21 |
| IL40133A (en) | 1975-03-13 |
| FR2150762A1 (enExample) | 1973-04-13 |
| DE2264979A1 (de) | 1976-01-15 |
| FR2150762B1 (enExample) | 1976-04-16 |
| DK131470C (enExample) | 1975-12-08 |
| IE36874L (en) | 1973-02-24 |
| DK131470B (da) | 1975-07-21 |
| NL149082B (nl) | 1976-04-15 |
| ES406367A1 (es) | 1975-07-01 |
| DE2264979B2 (de) | 1981-02-26 |
| BE787307A (fr) | 1972-12-01 |
| CA962677A (en) | 1975-02-11 |
| NO132761C (enExample) | 1975-12-29 |
| NO132761B (enExample) | 1975-09-22 |
| NL7211463A (enExample) | 1973-02-27 |
| DE2241241A1 (de) | 1973-03-15 |
| IE36874B1 (en) | 1977-03-16 |
| US3876639A (en) | 1975-04-08 |
| SE378599B (enExample) | 1975-09-08 |
| DE2264979C3 (de) | 1981-12-03 |
| ZA725626B (en) | 1973-05-30 |
| JPS4848493A (enExample) | 1973-07-09 |
| AT318626B (de) | 1974-11-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |