CH626345A5 - - Google Patents
Download PDFInfo
- Publication number
- CH626345A5 CH626345A5 CH877180A CH877180A CH626345A5 CH 626345 A5 CH626345 A5 CH 626345A5 CH 877180 A CH877180 A CH 877180A CH 877180 A CH877180 A CH 877180A CH 626345 A5 CH626345 A5 CH 626345A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- optically
- turning
- antipsychotic
- new
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- -1 piperidinylidene Chemical group 0.000 claims description 6
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical class C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 230000001078 anti-cholinergic effect Effects 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000001424 substituent group Chemical class 0.000 claims description 2
- 230000000561 anti-psychotic effect Effects 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 239000000164 antipsychotic agent Substances 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229910052740 iodine Chemical group 0.000 claims 3
- IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 2
- 229960001140 cyproheptadine Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000006340 racemization Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 230000003287 optical effect Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- GCRUXZKMBCLCMN-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-[2-(trifluoromethylsulfanyl)dibenzo[1,3-e:1',2'-f][7]annulen-11-ylidene]piperidine Chemical compound C12=CC(SC(F)(F)F)=CC=C2C=CC2=CC=CC=C2C1=C(CC1)CCN1CC1CC1 GCRUXZKMBCLCMN-UHFFFAOYSA-N 0.000 description 6
- 239000012458 free base Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- CMIBUZBMZCBCAT-HOTGVXAUSA-N (2s,3s)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@H](C(O)=O)[C@@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HOTGVXAUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NSACTPSEUXHIES-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-(2-iododibenzo[1,3-e:1',2'-f][7]annulen-11-ylidene)piperidine Chemical compound C12=CC(I)=CC=C2C=CC2=CC=CC=C2C1=C(CC1)CCN1CC1CC1 NSACTPSEUXHIES-UHFFFAOYSA-N 0.000 description 1
- WIZSJZJIFYLDAH-UHFFFAOYSA-N 1-cyclopropyl-2-methyl-4-[5-(trifluoromethylsulfanyl)-2-tricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,9,11,13-heptaenylidene]piperidine Chemical compound C1(CC1)N1C(CC(CC1)=C1C2=C(C=CC3=C1C=C(C=C3)SC(F)(F)F)C=CC=C2)C WIZSJZJIFYLDAH-UHFFFAOYSA-N 0.000 description 1
- NSFIAKFOCAEBER-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical compound C1=CC(C)=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 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
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- UCDWWJKPBQZZNT-UHFFFAOYSA-N magnesium;oxolane Chemical compound [Mg].C1CCOC1 UCDWWJKPBQZZNT-UHFFFAOYSA-N 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/72—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D211/74—Oxygen atoms
- C07D211/76—Oxygen atoms attached in position 2 or 6
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/02—Magnesium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/642,863 US4031222A (en) | 1975-12-22 | 1975-12-22 | Trifluoromethylthio (and sulfonyl) derivatives of cyproheptadine analogs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626345A5 true CH626345A5 (fr) | 1981-11-13 |
Family
ID=24578354
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1571276A CH625790A5 (fr) | 1975-12-22 | 1976-12-14 | |
| CH877080A CH626344A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH876980A CH626343A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH877180A CH626345A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH877280A CH626346A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH876880A CH627167A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH357381A CH631164A5 (de) | 1975-12-22 | 1981-06-01 | Verfahren zur herstellung von neuem 1-cyclopropylmethyl-4-(3-jod-5h-dibenzo(a,d)cyclohepten-5-yliden)piperidin. |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1571276A CH625790A5 (fr) | 1975-12-22 | 1976-12-14 | |
| CH877080A CH626344A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH876980A CH626343A5 (fr) | 1975-12-22 | 1980-11-26 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH877280A CH626346A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH876880A CH627167A5 (fr) | 1975-12-22 | 1980-11-26 | |
| CH357381A CH631164A5 (de) | 1975-12-22 | 1981-06-01 | Verfahren zur herstellung von neuem 1-cyclopropylmethyl-4-(3-jod-5h-dibenzo(a,d)cyclohepten-5-yliden)piperidin. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4031222A (fr) |
| JP (1) | JPS5278880A (fr) |
| AT (1) | AT363936B (fr) |
| AU (1) | AU506996B2 (fr) |
| BE (1) | BE849678A (fr) |
| CA (1) | CA1085823A (fr) |
| CH (7) | CH625790A5 (fr) |
| DE (1) | DE2657978C3 (fr) |
| DK (1) | DK550976A (fr) |
| ES (6) | ES454468A1 (fr) |
| FI (1) | FI763545A (fr) |
| FR (1) | FR2336133A1 (fr) |
| GB (1) | GB1519080A (fr) |
| GR (1) | GR62010B (fr) |
| HU (1) | HU175018B (fr) |
| IE (1) | IE44362B1 (fr) |
| IL (1) | IL51103A (fr) |
| LU (1) | LU76382A1 (fr) |
| NL (1) | NL7613713A (fr) |
| NO (1) | NO146359C (fr) |
| NZ (1) | NZ182868A (fr) |
| PH (1) | PH14088A (fr) |
| PL (4) | PL116941B1 (fr) |
| PT (1) | PT65956B (fr) |
| SE (1) | SE7613796L (fr) |
| ZA (1) | ZA767579B (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4148903A (en) * | 1977-07-28 | 1979-04-10 | Merck & Co., Inc. | Antipsychotic, antiserotonin and antihistaminic pyrrolo[2,1-b][3]benzazepines |
| US4132796A (en) * | 1977-12-01 | 1979-01-02 | Merck & Co., Inc. | Antipsychotic 3-trifluoromethylsulfinyl analogs of cyproheptadine |
| US4285956A (en) * | 1978-05-12 | 1981-08-25 | Kefalas A/S | Xanthene and thioxanthene derivatives, compositions thereof and treatment therewith |
| US4195091A (en) * | 1978-11-15 | 1980-03-25 | Merck & Co., Inc. | Appetite stimulating pyrrolo[2,1-b][3]benzazepines |
| EP0012988B1 (fr) * | 1979-01-02 | 1983-04-27 | Merck & Co. Inc. | Enantiomères lévogyres et dextrogyres de 3-halocyproheptadines, procédé pour leur préparation et composition pharmaceutique les contenant |
| US4275070A (en) * | 1979-05-21 | 1981-06-23 | Merck & Co., Inc. | Antipsychotic pharmaceutical compositions of the levorotatory enantiomers of 3-methoxycyproheptadine and an analog thereof |
| EP0019797A1 (fr) * | 1979-05-21 | 1980-12-10 | Merck & Co. Inc. | Enantiomères lévogyres et dextrogyres de 3-méthoxycyproheptadine et leurs analogues, procédé pour leur préparation et compositions pharmaceutiques à activité antipsychotique |
| US4220651A (en) * | 1979-05-21 | 1980-09-02 | Merck & Co., Inc. | Antipsychotic levorotatory enantiomers of 3-halocyproheptadines, analogs and derivatives |
| US5231105A (en) * | 1987-06-02 | 1993-07-27 | Ajinomoto Co., Inc. | Ethylamine derivatives and antihypertensives containing the same |
| US5250681A (en) * | 1988-06-02 | 1993-10-05 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| US5393890A (en) * | 1988-06-02 | 1995-02-28 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
| US5021426A (en) * | 1990-02-26 | 1991-06-04 | Merck & Co., Inc. | Method of traeting malaria with cyproheptadine derivatives |
| US5114919A (en) * | 1990-02-26 | 1992-05-19 | Merck & Co., Inc. | Adjuncts in cancer chemotherapy |
| US4996321A (en) * | 1990-02-26 | 1991-02-26 | Merck & Co., Inc. | Dibenzo[a,d]cycloheptenylidene compounds |
| CN103130708B (zh) * | 2011-12-01 | 2016-08-10 | 上海药明康德新药开发有限公司 | 一种n-叔丁氧羰基-4-硝基哌啶的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3851059A (en) * | 1970-02-05 | 1974-11-26 | Merck & Co Inc | Method for the stimulation of appetite in patients |
-
1975
- 1975-12-22 US US05/642,863 patent/US4031222A/en not_active Expired - Lifetime
-
1976
- 1976-12-08 DK DK550976A patent/DK550976A/da unknown
- 1976-12-08 SE SE7613796A patent/SE7613796L/xx not_active Application Discontinuation
- 1976-12-09 NL NL7613713A patent/NL7613713A/xx unknown
- 1976-12-09 FI FI763545A patent/FI763545A/fi not_active Application Discontinuation
- 1976-12-09 NO NO764188A patent/NO146359C/no unknown
- 1976-12-13 PT PT65956A patent/PT65956B/pt unknown
- 1976-12-13 NZ NZ182868A patent/NZ182868A/xx unknown
- 1976-12-13 HU HU76ME2035A patent/HU175018B/hu unknown
- 1976-12-14 IL IL51103A patent/IL51103A/xx unknown
- 1976-12-14 CH CH1571276A patent/CH625790A5/de not_active IP Right Cessation
- 1976-12-14 LU LU76382A patent/LU76382A1/xx unknown
- 1976-12-14 AU AU20528/76A patent/AU506996B2/en not_active Expired
- 1976-12-16 GR GR52418A patent/GR62010B/el unknown
- 1976-12-16 FR FR7637940A patent/FR2336133A1/fr active Granted
- 1976-12-16 GB GB52626/76A patent/GB1519080A/en not_active Expired
- 1976-12-16 CA CA267,998A patent/CA1085823A/fr not_active Expired
- 1976-12-17 IE IE2771/76A patent/IE44362B1/en unknown
- 1976-12-20 AT AT0943376A patent/AT363936B/de not_active IP Right Cessation
- 1976-12-20 PL PL1976222975A patent/PL116941B1/pl unknown
- 1976-12-20 PL PL1976222973A patent/PL116947B1/pl unknown
- 1976-12-20 PL PL1976194577A patent/PL116346B1/pl unknown
- 1976-12-20 PL PL1976222974A patent/PL122145B1/pl unknown
- 1976-12-21 DE DE2657978A patent/DE2657978C3/de not_active Expired
- 1976-12-21 PH PH19273A patent/PH14088A/en unknown
- 1976-12-21 ES ES454468A patent/ES454468A1/es not_active Expired
- 1976-12-21 ZA ZA00767579A patent/ZA767579B/xx unknown
- 1976-12-21 BE BE173486A patent/BE849678A/fr not_active IP Right Cessation
- 1976-12-22 JP JP51153529A patent/JPS5278880A/ja active Pending
-
1978
- 1978-02-01 ES ES466553A patent/ES466553A1/es not_active Expired
- 1978-02-01 ES ES466550A patent/ES466550A1/es not_active Expired
- 1978-02-01 ES ES466549A patent/ES466549A1/es not_active Expired
- 1978-02-01 ES ES466552A patent/ES466552A1/es not_active Expired
- 1978-02-01 ES ES466551A patent/ES466551A1/es not_active Expired
-
1980
- 1980-11-26 CH CH877080A patent/CH626344A5/de not_active IP Right Cessation
- 1980-11-26 CH CH876980A patent/CH626343A5/de not_active IP Right Cessation
- 1980-11-26 CH CH877180A patent/CH626345A5/de not_active IP Right Cessation
- 1980-11-26 CH CH877280A patent/CH626346A5/de not_active IP Right Cessation
- 1980-11-26 CH CH876880A patent/CH627167A5/de not_active IP Right Cessation
-
1981
- 1981-06-01 CH CH357381A patent/CH631164A5/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69810498T2 (de) | Ace-inhibitoren stickstoffsalze | |
| CH626345A5 (fr) | ||
| DD235638A5 (de) | Neue neuromuskulaere blockierungsmittel | |
| DE2437610A1 (de) | Neue 5,9-beta-disubstituierte 2-tetrahydrofurfuryl-6,7-benzomorphane, deren saeureadditionssalze, ihre verwendung als arzneimittel und verfahren zu deren herstellung | |
| DE10162375A1 (de) | Bicyclische N-Aryl-amide | |
| DD299431A5 (de) | Neue 2-oxo-3,8-diaza-spiro[4,5]dekan-derivate und verfahren zur herstellung dieser verbindungen | |
| DE10211416A1 (de) | Essig- und Propionsäureamide | |
| DD300105A5 (de) | Neue R(-)3-Quinuliclidinol - Derivate | |
| DE68905363T2 (de) | Heterotetracyclische laktamderivate, verfahren zu ihrer herstellung und pharmazeutische zubereitungen, die sie enthalten. | |
| EP0158956B1 (fr) | 4-(Nitrophényl)-tétrahydropyridines, leur procédé de préparation et leur application comme médicaments | |
| AT390954B (de) | Verfahren zur herstellung des neuen (-)-1beta|thyl-1alpha-(hydroxymethyl)-1,2,3,4,6,7,12, 12b alpha-octahydroindolo(2,3-a) chinolizins und von dessen saeureadditionssalzen | |
| DE69615845T2 (de) | Polycyclische alkaloid-derivate als nmda-rezeptor-antagonisten | |
| DE2632118A1 (de) | Apovincaminolester und verfahren zu deren herstellung | |
| DE10162442A1 (de) | Monocyclische N-Aryl-amide | |
| CH625789A5 (fr) | ||
| DE2719607A1 (de) | Benzodiazepine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2729165A1 (de) | Neue derivate der phenaethylamine, deren salze, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE3789411T2 (de) | Dihydropyridin-5-phosphonsaure zyklische Ester. | |
| DE2751905C2 (fr) | ||
| DE2748794C2 (de) | Malonylharnstoffkomplexe, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zusammensetzungen | |
| DE2848926A1 (de) | Neue derivate des isochinolins, ihre herstellung und die sie enthaltenden zusammensetzungen | |
| DE102004002885B4 (de) | Neue medizinisch einsetzbare Pyrrolalkaloide: Verfahren zu ihrer Isolierung, Synthese, sie enthaltende Arzneimittel und deren Verwendung | |
| DE2541434A1 (de) | 5-endo-(3-indolcarbonyloxy)-n- eckige klammer auf amino(niedrig)alkyl eckige klammer zu bicyclo eckige klammer auf 2.2.1 eckige klammer zu -heptan-2,3-di- endo-carbonsaeureimide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| CH675721A5 (fr) | ||
| DE3239789A1 (de) | Neue 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydropyridazinderivate, deren herstellung und pharmazeutische zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |