DE2302970C3 - Verfahren zur Herstellung von 4-(1-subst.-4-piperidyliden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10(9H)-onen - Google Patents
Verfahren zur Herstellung von 4-(1-subst.-4-piperidyliden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10(9H)-onenInfo
- Publication number
- DE2302970C3 DE2302970C3 DE2302970A DE2302970A DE2302970C3 DE 2302970 C3 DE2302970 C3 DE 2302970C3 DE 2302970 A DE2302970 A DE 2302970A DE 2302970 A DE2302970 A DE 2302970A DE 2302970 C3 DE2302970 C3 DE 2302970C3
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- general formula
- benzo
- cyclohepta
- thiophen
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 7
- -1 4- (1-substituted-4-piperidylidene) -4H-benzo [4,5] cyclohepta [1,2-b] thiophene-10 (9H) -ones Chemical class 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VOBWLFNYOWWARN-UHFFFAOYSA-N thiophen-3-one Chemical compound O=C1CSC=C1 VOBWLFNYOWWARN-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- MWWHYPORGYMFIP-UHFFFAOYSA-N cyclohepta[b]thiophen-4-one Chemical compound O=C1C=CC=CC2=C1C=CS2 MWWHYPORGYMFIP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000003747 Grignard reaction Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000003500 enol ether group Chemical group 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000004452 microanalysis Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 231100000820 toxicity test Toxicity 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002084 enol ethers Chemical class 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NCDLFYLLYQXPCS-UHFFFAOYSA-N 2-chloro-1-methylpiperidine Chemical compound CN1CCCCC1Cl NCDLFYLLYQXPCS-UHFFFAOYSA-N 0.000 description 1
- NFHHBIGYIAIGFH-UHFFFAOYSA-N 2h-cyclohepta[b]thiophene Chemical compound C1=CC=CC2=CCSC2=C1 NFHHBIGYIAIGFH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- AAYKXJAFSKIHRK-UHFFFAOYSA-N 4-methoxy-10-(1-methylpiperidin-4-yl)benzo[1,2]cyclohepta[3,4-b]thiophen-10-ol Chemical compound C1=2C=CSC=2C(OC)=CC2=CC=CC=C2C1(O)C1CCN(C)CC1 AAYKXJAFSKIHRK-UHFFFAOYSA-N 0.000 description 1
- ZSGIVIUNURDDJL-UHFFFAOYSA-N 4-methoxybenzo[1,2]cyclohepta[3,4-b]thiophen-10-one Chemical compound COC1=CC2=CC=CC=C2C(=O)C2=C1SC=C2 ZSGIVIUNURDDJL-UHFFFAOYSA-N 0.000 description 1
- 206010040108 Serotonin syndrome Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 230000001558 histaminolytic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- HERSKCAGZCXYMC-UHFFFAOYSA-N thiophen-3-ol Chemical compound OC=1C=CSC=1 HERSKCAGZCXYMC-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH98572A CH568312A5 (enExample) | 1972-01-24 | 1972-01-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2302970A1 DE2302970A1 (de) | 1973-08-02 |
| DE2302970B2 DE2302970B2 (de) | 1981-06-25 |
| DE2302970C3 true DE2302970C3 (de) | 1982-03-18 |
Family
ID=4199789
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2302970A Expired DE2302970C3 (de) | 1972-01-24 | 1973-01-22 | Verfahren zur Herstellung von 4-(1-subst.-4-piperidyliden)-4H-benzo [4,5] cyclohepta [1,2-b] thiophen-10(9H)-onen |
| DE2366394A Expired DE2366394C1 (de) | 1972-01-24 | 1973-01-22 | 4H-Benzo [4,5] cyclohepta [1,2-b] thiophen-4-one und deren Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2366394A Expired DE2366394C1 (de) | 1972-01-24 | 1973-01-22 | 4H-Benzo [4,5] cyclohepta [1,2-b] thiophen-4-one und deren Herstellung |
Country Status (29)
| Country | Link |
|---|---|
| JP (2) | JPS566997B2 (enExample) |
| KR (1) | KR780000049B1 (enExample) |
| AR (1) | AR202094A1 (enExample) |
| AT (1) | AT334897B (enExample) |
| AU (1) | AU477308B2 (enExample) |
| BE (1) | BE794370A (enExample) |
| CA (1) | CA1006523A (enExample) |
| CH (1) | CH568312A5 (enExample) |
| CS (1) | CS183674B2 (enExample) |
| DD (1) | DD104084A5 (enExample) |
| DE (2) | DE2302970C3 (enExample) |
| DK (2) | DK154296C (enExample) |
| ES (1) | ES410855A1 (enExample) |
| FI (1) | FI60396C (enExample) |
| FR (2) | FR2169091B1 (enExample) |
| GB (2) | GB1422443A (enExample) |
| HK (1) | HK53480A (enExample) |
| HU (1) | HU164966B (enExample) |
| IE (1) | IE38148B1 (enExample) |
| IL (1) | IL41374A (enExample) |
| LU (1) | LU66876A1 (enExample) |
| NL (1) | NL178970C (enExample) |
| NO (1) | NO136978C (enExample) |
| PL (1) | PL83921B1 (enExample) |
| RO (1) | RO63566A (enExample) |
| SE (1) | SE395696B (enExample) |
| SU (1) | SU509237A3 (enExample) |
| YU (1) | YU36173B (enExample) |
| ZA (1) | ZA73494B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2243778T3 (en) * | 2008-01-30 | 2014-11-17 | Nippon Zoki Pharmaceutical Co | piperidine |
| PT2319840E (pt) * | 2008-08-01 | 2016-02-10 | Nippon Zoki Pharmaceutical Co | Derivado de aminopropilideno |
| JP5083989B2 (ja) * | 2008-11-20 | 2012-11-28 | 日本臓器製薬株式会社 | ピペリジン誘導体を含有する医薬 |
| CN104817532B (zh) * | 2015-03-04 | 2017-07-25 | 浙江工业大学 | 一种10‑甲氧基‑4H‑苯并[4,5]环庚三烯[1,2‑b]噻唑‑4‑酮的制备方法 |
-
1972
- 1972-01-24 CH CH98572A patent/CH568312A5/xx not_active IP Right Cessation
-
1973
- 1973-01-12 FI FI89/73A patent/FI60396C/fi active
- 1973-01-15 SE SE7300504A patent/SE395696B/xx unknown
- 1973-01-16 NO NO185/73A patent/NO136978C/no unknown
- 1973-01-19 FR FR7301856A patent/FR2169091B1/fr not_active Expired
- 1973-01-19 NL NLAANVRAGE7300797,A patent/NL178970C/xx not_active IP Right Cessation
- 1973-01-22 BE BE794370D patent/BE794370A/xx not_active IP Right Cessation
- 1973-01-22 DE DE2302970A patent/DE2302970C3/de not_active Expired
- 1973-01-22 ES ES410855A patent/ES410855A1/es not_active Expired
- 1973-01-22 DE DE2366394A patent/DE2366394C1/de not_active Expired
- 1973-01-22 DD DD168384A patent/DD104084A5/xx unknown
- 1973-01-22 AT AT47873*#A patent/AT334897B/de not_active IP Right Cessation
- 1973-01-22 KR KR7300110A patent/KR780000049B1/ko not_active Expired
- 1973-01-22 GB GB311973A patent/GB1422443A/en not_active Expired
- 1973-01-22 PL PL1973160372A patent/PL83921B1/pl unknown
- 1973-01-22 CA CA161,801A patent/CA1006523A/en not_active Expired
- 1973-01-22 HU HUSA2446A patent/HU164966B/hu unknown
- 1973-01-22 LU LU66876A patent/LU66876A1/xx unknown
- 1973-01-22 IE IE90/73A patent/IE38148B1/xx unknown
- 1973-01-22 RO RO7300073573A patent/RO63566A/ro unknown
- 1973-01-22 GB GB2921475A patent/GB1422444A/en not_active Expired
- 1973-01-23 JP JP922773A patent/JPS566997B2/ja not_active Expired
- 1973-01-23 CS CS7300000503A patent/CS183674B2/cs unknown
- 1973-01-23 ZA ZA730494A patent/ZA73494B/xx unknown
- 1973-01-23 IL IL41374A patent/IL41374A/en unknown
- 1973-01-23 AU AU51378/73A patent/AU477308B2/en not_active Expired
- 1973-01-23 SU SU1874878A patent/SU509237A3/ru active
- 1973-01-27 AR AR246230A patent/AR202094A1/es active
- 1973-04-22 YU YU178/73A patent/YU36173B/xx unknown
-
1978
- 1978-10-04 FR FR7828336A patent/FR2401153A1/fr active Granted
-
1980
- 1980-02-29 JP JP2420780A patent/JPS55129282A/ja active Granted
- 1980-09-25 HK HK534/80A patent/HK53480A/xx unknown
- 1980-12-29 DK DK555680A patent/DK154296C/da not_active IP Right Cessation
-
1990
- 1990-10-02 DK DK238090A patent/DK161324C/da not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OD | Request for examination | ||
| AH | Division in |
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