DE2235998C3 - Phenothiazinderivate, ihre Herstellung und die pharmazeutischen Zusammensetzungen, die sie enthalten - Google Patents
Phenothiazinderivate, ihre Herstellung und die pharmazeutischen Zusammensetzungen, die sie enthaltenInfo
- Publication number
- DE2235998C3 DE2235998C3 DE19722235998 DE2235998A DE2235998C3 DE 2235998 C3 DE2235998 C3 DE 2235998C3 DE 19722235998 DE19722235998 DE 19722235998 DE 2235998 A DE2235998 A DE 2235998A DE 2235998 C3 DE2235998 C3 DE 2235998C3
- Authority
- DE
- Germany
- Prior art keywords
- phenothiazine
- general formula
- carbamoyl
- piperidine
- dimethylsulfamoyl
- 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
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 title claims description 3
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 23
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 238000000034 method Methods 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 229950000688 phenothiazine Drugs 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
- -1 for example Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- CAIRIHSMGHHLNM-UHFFFAOYSA-N CN(C)S(=O)(=O)C1=CC=C2N(CCCCl)C3=CC=CC=C3SC2=C1 Chemical compound CN(C)S(=O)(=O)C1=CC=C2N(CCCCl)C3=CC=CC=C3SC2=C1 CAIRIHSMGHHLNM-UHFFFAOYSA-N 0.000 description 7
- 150000002990 phenothiazines Chemical class 0.000 description 7
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 5
- NCPHGZWGGANCAY-UHFFFAOYSA-N methane;ruthenium Chemical compound C.[Ru] NCPHGZWGGANCAY-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000003474 anti-emetic effect Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- JQFRWECADGVDCA-UHFFFAOYSA-N CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCCl Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCCl JQFRWECADGVDCA-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- PTHRNTMWAVLJQM-UHFFFAOYSA-N n-(1-hydroxypropan-2-yl)piperidine-4-carboxamide Chemical compound OCC(C)NC(=O)C1CCNCC1 PTHRNTMWAVLJQM-UHFFFAOYSA-N 0.000 description 3
- SASXKISDCPJSKJ-UHFFFAOYSA-N n-(2-hydroxypropyl)piperidine-4-carboxamide Chemical compound CC(O)CNC(=O)C1CCNCC1 SASXKISDCPJSKJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000009132 Catalepsy Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 206010047853 Waxy flexibility Diseases 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 230000003354 anti-apomorphinic effect Effects 0.000 description 2
- 239000002111 antiemetic agent Substances 0.000 description 2
- 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 2
- 229960004046 apomorphine Drugs 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000002903 catalepsic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- UTNUSSVWENUMCJ-UHFFFAOYSA-N n,n-dimethyl-10h-phenothiazine-3-sulfonamide Chemical compound C1=CC=C2SC3=CC(S(=O)(=O)N(C)C)=CC=C3NC2=C1 UTNUSSVWENUMCJ-UHFFFAOYSA-N 0.000 description 2
- LJAFMUPWFJJGOA-UHFFFAOYSA-N n-(2-hydroxy-2-methylpropyl)piperidine-4-carboxamide Chemical compound CC(C)(O)CNC(=O)C1CCNCC1 LJAFMUPWFJJGOA-UHFFFAOYSA-N 0.000 description 2
- SGUNZEMSKPUFDM-UHFFFAOYSA-N n-(2-hydroxyethyl)piperidine-4-carboxamide Chemical compound OCCNC(=O)C1CCNCC1 SGUNZEMSKPUFDM-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- DLCIJMPSJTVVHJ-UHFFFAOYSA-N 10-(3-chloropropyl)phenothiazine Chemical compound C1=CC=C2N(CCCCl)C3=CC=CC=C3SC2=C1 DLCIJMPSJTVVHJ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- AGVHHIPLRYPZKP-UHFFFAOYSA-N C(C(=O)O)(=O)O.CN(S(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN1CCC(CC1)C(NCCO)=O)C Chemical compound C(C(=O)O)(=O)O.CN(S(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN1CCC(CC1)C(NCCO)=O)C AGVHHIPLRYPZKP-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- VUBIAYNSGZMVCM-UHFFFAOYSA-N N-(2-hydroxyethyl)-1-[3-(3-methylsulfonylphenothiazin-10-yl)propyl]piperidine-4-carboxamide Chemical compound CS(=O)(=O)C=1C=CC=2N(C3=CC=CC=C3SC2C1)CCCN1CCC(CC1)C(NCCO)=O VUBIAYNSGZMVCM-UHFFFAOYSA-N 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229940125683 antiemetic agent Drugs 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 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
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OYQCAKVBGOQZFE-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylpiperidine-4-carboxamide Chemical compound OCCN(C)C(=O)C1CCNCC1 OYQCAKVBGOQZFE-UHFFFAOYSA-N 0.000 description 1
- AQXRBEHWQCOKJI-UHFFFAOYSA-N n-(2-hydroxypropyl)pyridine-4-carboxamide Chemical compound CC(O)CNC(=O)C1=CC=NC=C1 AQXRBEHWQCOKJI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent 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
- 238000012360 testing method Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- XCTYLCDETUVOIP-UHFFFAOYSA-N thiethylperazine Chemical compound C12=CC(SCC)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(C)CC1 XCTYLCDETUVOIP-UHFFFAOYSA-N 0.000 description 1
- 229960004869 thiethylperazine Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7126709A FR2146150B1 (enExample) | 1971-07-21 | 1971-07-21 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2235998A1 DE2235998A1 (de) | 1973-02-01 |
| DE2235998B2 DE2235998B2 (de) | 1981-04-02 |
| DE2235998C3 true DE2235998C3 (de) | 1982-01-07 |
Family
ID=9080680
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722235998 Expired DE2235998C3 (de) | 1971-07-21 | 1972-07-21 | Phenothiazinderivate, ihre Herstellung und die pharmazeutischen Zusammensetzungen, die sie enthalten |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5619349B1 (enExample) |
| AR (2) | AR193118A1 (enExample) |
| AT (1) | AT317234B (enExample) |
| AU (1) | AU458571B2 (enExample) |
| BE (1) | BE786583A (enExample) |
| CH (1) | CH541578A (enExample) |
| DE (1) | DE2235998C3 (enExample) |
| ES (2) | ES405048A1 (enExample) |
| FR (1) | FR2146150B1 (enExample) |
| GB (1) | GB1333700A (enExample) |
| NL (1) | NL7209698A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104884064A (zh) | 2012-12-24 | 2015-09-02 | 纽洛佳斯特拉斯公司 | 用于治疗胃肠道病症的方法 |
| US9844554B2 (en) * | 2014-06-24 | 2017-12-19 | Neurogastrx, Inc. | Prodrugs of metopimazine |
| US10836757B1 (en) | 2020-04-02 | 2020-11-17 | Neurogastrx, Inc. | Polymorphic forms of metopimazine |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL99690C (enExample) * | 1956-11-15 | |||
| DE1092476B (de) * | 1958-04-24 | 1960-11-10 | Rhone Poulenc Sa | Verfahren zur Herstellung von Phenthiazinderivaten |
-
0
- BE BE786583D patent/BE786583A/xx unknown
-
1971
- 1971-07-21 FR FR7126709A patent/FR2146150B1/fr not_active Expired
-
1972
- 1972-07-13 NL NL7209698A patent/NL7209698A/xx not_active Application Discontinuation
- 1972-07-19 JP JP7243572A patent/JPS5619349B1/ja active Pending
- 1972-07-19 GB GB3377372A patent/GB1333700A/en not_active Expired
- 1972-07-19 AU AU44741/72A patent/AU458571B2/en not_active Expired
- 1972-07-20 CH CH1085572A patent/CH541578A/fr not_active IP Right Cessation
- 1972-07-21 ES ES405048A patent/ES405048A1/es not_active Expired
- 1972-07-21 DE DE19722235998 patent/DE2235998C3/de not_active Expired
- 1972-07-21 AR AR24320972A patent/AR193118A1/es active
- 1972-07-21 AT AT629772A patent/AT317234B/de not_active IP Right Cessation
- 1972-10-23 ES ES407867A patent/ES407867A1/es not_active Expired
-
1973
- 1973-01-15 AR AR24612373A patent/AR193181A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ES405048A1 (es) | 1975-07-16 |
| AT317234B (de) | 1974-08-26 |
| AR193118A1 (es) | 1973-03-30 |
| FR2146150A1 (enExample) | 1973-03-02 |
| CH541578A (fr) | 1973-09-15 |
| JPS5619349B1 (enExample) | 1981-05-07 |
| DE2235998B2 (de) | 1981-04-02 |
| GB1333700A (en) | 1973-10-10 |
| ES407867A1 (es) | 1975-11-16 |
| FR2146150B1 (enExample) | 1974-09-06 |
| DE2235998A1 (de) | 1973-02-01 |
| AR193181A1 (es) | 1973-03-30 |
| AU4474172A (en) | 1974-01-24 |
| BE786583A (fr) | 1973-01-22 |
| NL7209698A (enExample) | 1973-01-23 |
| AU458571B2 (en) | 1975-02-27 |
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