CH621786A5 - Process for the preparation of a novel behenic acid ester - Google Patents
Process for the preparation of a novel behenic acid ester Download PDFInfo
- Publication number
- CH621786A5 CH621786A5 CH1003576A CH1003576A CH621786A5 CH 621786 A5 CH621786 A5 CH 621786A5 CH 1003576 A CH1003576 A CH 1003576A CH 1003576 A CH1003576 A CH 1003576A CH 621786 A5 CH621786 A5 CH 621786A5
- Authority
- CH
- Switzerland
- Prior art keywords
- isomer
- behenic acid
- formula
- hydroxyethyl
- ester
- Prior art date
Links
- UKMSUNONTOPOIO-UHFFFAOYSA-N Behenic acid Natural products CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 title claims description 16
- -1 behenic acid ester Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 15
- 235000021357 Behenic acid Nutrition 0.000 title claims description 10
- 229940116226 behenic acid Drugs 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 231100000252 nontoxic Toxicity 0.000 claims description 9
- 230000003000 nontoxic effect Effects 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 7
- 239000012458 free base Substances 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QTHQYNCAWSGBCE-UHFFFAOYSA-N docosanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCCCCCC(Cl)=O QTHQYNCAWSGBCE-UHFFFAOYSA-N 0.000 claims 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- 238000012360 testing method Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000003176 neuroleptic agent Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 229940025084 amphetamine Drugs 0.000 description 5
- 229960004046 apomorphine Drugs 0.000 description 5
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- 230000000701 neuroleptic effect Effects 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 5
- 239000008158 vegetable oil Substances 0.000 description 5
- GDOBERVQHKPDKE-UHFFFAOYSA-N 2-[4-[3-[6-fluoro-2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperazin-1-yl]ethanol Chemical compound C1CN(CCO)CCN1CCC=C1C2=CC(C(F)(F)F)=CC=C2SC2=CC(F)=CC=C21 GDOBERVQHKPDKE-UHFFFAOYSA-N 0.000 description 4
- 235000021314 Palmitic acid Nutrition 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 206010047700 Vomiting Diseases 0.000 description 4
- 125000003450 decanoic acid ester group Chemical group 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- 230000008673 vomiting Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000032050 esterification Effects 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 229960002419 flupentixol Drugs 0.000 description 3
- 239000008174 sterile solution Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000005075 thioxanthenes Chemical class 0.000 description 3
- CCUOZZURYIZOKX-UHFFFAOYSA-N 2-[1-[3-[6-fluoro-2-(trifluoromethyl)thioxanthen-9-ylidene]propyl]piperidin-4-yl]ethanol Chemical compound C1CC(CCO)CCN1CCC=C1C2=CC(C(F)(F)F)=CC=C2SC2=CC(F)=CC=C21 CCUOZZURYIZOKX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 230000005923 long-lasting effect Effects 0.000 description 2
- 239000004006 olive oil Substances 0.000 description 2
- 235000008390 olive oil Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000008159 sesame oil Substances 0.000 description 2
- 235000011803 sesame oil Nutrition 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SKYZYDSNJIOXRL-BTQNPOSSSA-N (6ar)-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-10,11-diol;hydrochloride Chemical compound Cl.C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 SKYZYDSNJIOXRL-BTQNPOSSSA-N 0.000 description 1
- FSZCMOVQVXIAPA-UHFFFAOYSA-N 10-propylidene-9H-thioxanthene Chemical compound C(CC)=S1C=2C=CC=CC=2CC2=CC=CC=C12 FSZCMOVQVXIAPA-UHFFFAOYSA-N 0.000 description 1
- LDSQQXKSEFZAPE-UHFFFAOYSA-N 2-piperidin-4-ylethanol Chemical compound OCCC1CCNCC1 LDSQQXKSEFZAPE-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
- ZDGGCIXEWFPFAH-UHFFFAOYSA-N 6-fluoro-2-(trifluoromethyl)thioxanthen-9-one Chemical compound C1=C(C(F)(F)F)C=C2C(=O)C3=CC=C(F)C=C3SC2=C1 ZDGGCIXEWFPFAH-UHFFFAOYSA-N 0.000 description 1
- GRFZWXGOHAQNGF-UHFFFAOYSA-N 6-fluoro-9-prop-2-enylidene-2-(trifluoromethyl)thioxanthene Chemical compound FC(F)(F)C1=CC=C2SC3=CC(F)=CC=C3C(=CC=C)C2=C1 GRFZWXGOHAQNGF-UHFFFAOYSA-N 0.000 description 1
- RTZKSCVEACYZBQ-UHFFFAOYSA-N 6-fluoro-9-propan-2-ylidene-2-(trifluoromethyl)thioxanthene Chemical compound FC(C1=CC=2C(C3=CC=C(C=C3SC=2C=C1)F)=C(C)C)(F)F RTZKSCVEACYZBQ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 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
- 238000010521 absorption reaction Methods 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940008238 amphetamine sulfate Drugs 0.000 description 1
- PYHRZPFZZDCOPH-UHFFFAOYSA-N amphetamine sulfate Chemical compound OS(O)(=O)=O.CC(N)CC1=CC=CC=C1.CC(N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229960003990 apomorphine hydrochloride Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- UGMCXQCYOVCMTB-UHFFFAOYSA-K dihydroxy(stearato)aluminium Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[Al](O)O UGMCXQCYOVCMTB-UHFFFAOYSA-K 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000857 drug effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 210000004744 fore-foot Anatomy 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000004916 vomit Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/604,462 US4042695A (en) | 1972-12-08 | 1975-08-13 | Thiaxanthene derivatives, compositions thereof and methods of treating therewith |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621786A5 true CH621786A5 (en) | 1981-02-27 |
Family
ID=24419699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1003576A CH621786A5 (en) | 1975-08-13 | 1976-08-05 | Process for the preparation of a novel behenic acid ester |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5239682A (sv) |
| AT (1) | AT345826B (sv) |
| AU (1) | AU500540B2 (sv) |
| BE (1) | BE845057A (sv) |
| CH (1) | CH621786A5 (sv) |
| DE (1) | DE2631389A1 (sv) |
| DK (1) | DK363476A (sv) |
| ES (1) | ES450128A1 (sv) |
| FI (1) | FI60008C (sv) |
| FR (1) | FR2320740A1 (sv) |
| GB (1) | GB1498394A (sv) |
| HU (1) | HU171915B (sv) |
| IE (1) | IE43413B1 (sv) |
| NL (1) | NL7608822A (sv) |
| NO (1) | NO762748L (sv) |
| PL (1) | PL98033B1 (sv) |
| SE (1) | SE7607300L (sv) |
| ZA (1) | ZA764544B (sv) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5474109A (en) * | 1977-11-25 | 1979-06-14 | Jiyushi Insatsushiya Yuugen | Method and device for screen printing |
| JPS5481904A (en) * | 1977-12-09 | 1979-06-29 | Horii & Co Ltd | Method of printing with perforated plate |
| JPS5559990A (en) * | 1978-10-30 | 1980-05-06 | Horii Toushiyadou Kk | Mimeographing method |
| US4368190A (en) | 1980-04-17 | 1983-01-11 | Merck & Co., Inc. | Immunologically active dipeptidyl 4-O-,6-O-acyl-2-amino-2-deoxy-D-glucose derivatives and methods for their preparation |
| JPS57191005A (en) * | 1981-05-22 | 1982-11-24 | Sumikichi Inoue | Manufacture of ceramic |
| GB8628903D0 (en) * | 1986-12-03 | 1987-01-07 | Lunbeck A S H | Neuroleptic compounds |
-
1976
- 1976-06-24 SE SE7607300A patent/SE7607300L/sv unknown
- 1976-07-13 DE DE19762631389 patent/DE2631389A1/de not_active Withdrawn
- 1976-07-15 AT AT519676A patent/AT345826B/de not_active IP Right Cessation
- 1976-07-24 ES ES450128A patent/ES450128A1/es not_active Expired
- 1976-07-27 GB GB31328/76A patent/GB1498394A/en not_active Expired
- 1976-07-28 ZA ZA764544A patent/ZA764544B/xx unknown
- 1976-07-29 FI FI762172A patent/FI60008C/fi not_active IP Right Cessation
- 1976-08-03 AU AU16515/76A patent/AU500540B2/en not_active Expired
- 1976-08-04 IE IE1719/76A patent/IE43413B1/en unknown
- 1976-08-05 CH CH1003576A patent/CH621786A5/de not_active IP Right Cessation
- 1976-08-06 HU HU76KE00000992A patent/HU171915B/hu unknown
- 1976-08-06 NO NO762748A patent/NO762748L/no unknown
- 1976-08-09 NL NL7608822A patent/NL7608822A/xx unknown
- 1976-08-10 JP JP51094572A patent/JPS5239682A/ja active Pending
- 1976-08-10 BE BE169705A patent/BE845057A/xx unknown
- 1976-08-12 DK DK363476A patent/DK363476A/da unknown
- 1976-08-12 PL PL1976191771A patent/PL98033B1/pl unknown
- 1976-08-13 FR FR7624832A patent/FR2320740A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES450128A1 (es) | 1977-12-01 |
| GB1498394A (en) | 1978-01-18 |
| DK363476A (da) | 1977-02-14 |
| HU171915B (hu) | 1978-04-28 |
| FI762172A (sv) | 1977-02-14 |
| AU500540B2 (en) | 1979-05-24 |
| ZA764544B (en) | 1977-07-27 |
| IE43413L (en) | 1977-02-13 |
| AU1651576A (en) | 1978-02-09 |
| DE2631389A1 (de) | 1977-02-24 |
| FI60008B (fi) | 1981-07-31 |
| FR2320740B1 (sv) | 1981-03-27 |
| FR2320740A1 (fr) | 1977-03-11 |
| PL98033B1 (pl) | 1978-04-29 |
| BE845057A (fr) | 1977-02-10 |
| NL7608822A (nl) | 1977-02-15 |
| IE43413B1 (en) | 1981-02-25 |
| ATA519676A (de) | 1978-02-15 |
| NO762748L (sv) | 1977-02-15 |
| FI60008C (fi) | 1981-11-10 |
| AT345826B (de) | 1978-10-10 |
| JPS5239682A (en) | 1977-03-28 |
| SE7607300L (sv) | 1977-02-14 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |