CH657136A5 - Carboxamidoderivate von 5h-1,3,4-thiadiazolo-(3,2-a)-pyrimidinen und verfahren zu ihrer herstellung. - Google Patents
Carboxamidoderivate von 5h-1,3,4-thiadiazolo-(3,2-a)-pyrimidinen und verfahren zu ihrer herstellung. Download PDFInfo
- Publication number
- CH657136A5 CH657136A5 CH6783/83A CH678383A CH657136A5 CH 657136 A5 CH657136 A5 CH 657136A5 CH 6783/83 A CH6783/83 A CH 6783/83A CH 678383 A CH678383 A CH 678383A CH 657136 A5 CH657136 A5 CH 657136A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridyl
- oxo
- carboxamide
- thiadiazolo
- pyrimidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- -1 2-methylmorpholino Chemical group 0.000 claims description 97
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 26
- 125000004076 pyridyl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 150000003857 carboxamides Chemical class 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000815 N-oxide group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 238000001816 cooling Methods 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 239000005457 ice water Substances 0.000 description 13
- 229920000137 polyphosphoric acid Polymers 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 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 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000005389 trialkylsiloxy group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
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- 239000013543 active substance Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
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- 239000008096 xylene Substances 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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- 238000007796 conventional method Methods 0.000 description 3
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- 238000000354 decomposition reaction Methods 0.000 description 3
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- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- YGJPOWJYFUMPBX-UHFFFAOYSA-N 2-pyridin-4-yl-[1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one Chemical compound N1=CC=C(C=C1)C1=NN2C(=NC=CC2=O)S1 YGJPOWJYFUMPBX-UHFFFAOYSA-N 0.000 description 2
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- PWVGMQFTWJTCNG-UHFFFAOYSA-N thiadiazolo[5,4-d]pyrimidine Chemical class C1=NC=C2N=NSC2=N1 PWVGMQFTWJTCNG-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8236642 | 1982-12-23 | ||
| GB838329746A GB8329746D0 (en) | 1983-11-08 | 1983-11-08 | Carboxamido-derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH657136A5 true CH657136A5 (de) | 1986-08-15 |
Family
ID=26284768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6783/83A CH657136A5 (de) | 1982-12-23 | 1983-12-20 | Carboxamidoderivate von 5h-1,3,4-thiadiazolo-(3,2-a)-pyrimidinen und verfahren zu ihrer herstellung. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4522944A (cg-RX-API-DMAC7.html) |
| AT (1) | AT385036B (cg-RX-API-DMAC7.html) |
| AU (1) | AU558600B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1211440A (cg-RX-API-DMAC7.html) |
| CH (1) | CH657136A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3346223A1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK593983A (cg-RX-API-DMAC7.html) |
| FI (1) | FI834698A7 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2538392B1 (cg-RX-API-DMAC7.html) |
| GR (1) | GR79479B (cg-RX-API-DMAC7.html) |
| IL (1) | IL70522A (cg-RX-API-DMAC7.html) |
| IT (1) | IT1194521B (cg-RX-API-DMAC7.html) |
| NL (1) | NL8304340A (cg-RX-API-DMAC7.html) |
| SE (1) | SE454698B (cg-RX-API-DMAC7.html) |
| SU (1) | SU1297731A3 (cg-RX-API-DMAC7.html) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3702758A1 (de) * | 1987-01-30 | 1988-09-29 | Hoechst Ag | Substituierte 3-phenyl-7h-thiazolo (3,2-b) (1,2,4) triazin-7-one, verfahren zu ihrer herstellung, die sie enthaltenden arzneimittel und ihre verwendung, sowie einige bei der herstellung der genannten verbindungen gebildete zwischenprodukte |
| CA2679754C (en) | 2007-03-12 | 2018-08-07 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines synthesis |
| US9428506B2 (en) | 2012-04-14 | 2016-08-30 | Intra-Cellular Therapies, Inc. | Substituted pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxalines for the treatment of nervous system disorders |
| EP2968320B1 (en) | 2013-03-15 | 2020-11-11 | Intra-Cellular Therapies, Inc. | Organic compounds |
| DK3076967T3 (da) | 2013-12-03 | 2021-10-25 | Intra Cellular Therapies Inc | Fremgangsmåder til behandling af residuelle symptomer på skizofreni |
| MX2016013046A (es) | 2014-04-04 | 2017-02-15 | Intra Cellular Therapies Inc | Compuestos organicos. |
| CN106535898A (zh) | 2014-04-04 | 2017-03-22 | 细胞内治疗公司 | 有机化合物 |
| PL3838274T3 (pl) | 2016-01-26 | 2024-04-02 | Intra-Cellular Therapies, Inc. | Pochodna pirydo[3',4':4,5]pirolo[1,2,3-DE]chinoksaliny do zastosowania w leczeniu zaburzeń OUN |
| WO2017172784A1 (en) | 2016-03-28 | 2017-10-05 | Intra-Cellular Therapies, Inc. | Novel salts and crystals |
| JP2019510039A (ja) | 2016-03-28 | 2019-04-11 | イントラ−セルラー・セラピーズ・インコーポレイテッドＩｎｔｒａ−Ｃｅｌｌｕｌａｒ Ｔｈｅｒａｐｉｅｓ， Ｉｎｃ． | 新規組成物および方法 |
| US11014925B2 (en) | 2016-03-28 | 2021-05-25 | Intra-Cellular Therapies, Inc. | Co-crystals of 1-(4-fluoro-phenyl)-4-((6bR,1OaS)-3-methyl-2,3,6b,9,10,10a-hexahydro-1H,7H- pyrido[3′,4′:4,51_pyrrolo [1,2,3-delqcuinoxalin-8-yl)-butan-1-one with nicotinamide or isonicotinamide |
| US11331316B2 (en) | 2016-10-12 | 2022-05-17 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
| EP3562484B1 (en) | 2016-12-29 | 2021-08-25 | Intra-Cellular Therapies, Inc. | Pyrido[3',4':4,5]pyrrolo[1,2,3-de]quinoxaline derivatives useful in the treatment of cns disorders |
| US10961245B2 (en) | 2016-12-29 | 2021-03-30 | Intra-Cellular Therapies, Inc. | Substituted heterocycle fused gamma-carbolines for treatment of central nervous system disorders |
| RU2767410C2 (ru) | 2017-03-24 | 2022-03-17 | Интра-Селлулар Терапиз, Инк. | Новые композиции и способы |
| KR102667268B1 (ko) | 2017-07-26 | 2024-05-17 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| EP3658145A4 (en) | 2017-07-26 | 2021-04-21 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| CN112040940A (zh) | 2018-03-23 | 2020-12-04 | 细胞内治疗公司 | 有机化合物 |
| CN112384218B (zh) | 2018-06-06 | 2024-04-26 | 细胞内治疗公司 | 盐和晶体 |
| ES3028377T3 (en) | 2018-06-08 | 2025-06-19 | Intra Cellular Therapies Inc | Fused gamma-carbolines for acute treatment of anxiety or depression |
| KR20250034203A (ko) | 2018-06-11 | 2025-03-10 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| JP2022500362A (ja) | 2018-08-29 | 2022-01-04 | イントラ−セルラー・セラピーズ・インコーポレイテッドIntra−Cellular Therapies, Inc. | 新規組成物および方法 |
| AU2019331490B2 (en) | 2018-08-31 | 2025-04-24 | Intra-Cellular Therapies, Inc. | Novel methods |
| CA3108553A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| EP4134101A1 (en) | 2019-07-07 | 2023-02-15 | Intra-Cellular Therapies, Inc. | Deuterated lumateperone for the treatment of the bipolar ii disorder |
| JP7261942B2 (ja) | 2019-12-11 | 2023-04-20 | イントラ－セルラー・セラピーズ・インコーポレイテッド | 有機化合物 |
| US12414948B2 (en) | 2022-05-18 | 2025-09-16 | Intra-Cellular Therapies, Inc. | Methods |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5129981B2 (cg-RX-API-DMAC7.html) * | 1973-07-17 | 1976-08-28 | ||
| GB1568962A (en) * | 1975-10-31 | 1980-06-11 | Beecham Group Ltd | Reparation and compositions containing them (heterocyclic-carbonylamino)pencillins methods for their p |
| JPS55115889A (en) * | 1979-02-28 | 1980-09-06 | Teijin Ltd | 6-carbamoylthiazolo 3,2-a pyrimidine derivative and its preparation |
| JPS57142989A (en) * | 1981-02-27 | 1982-09-03 | Dai Ichi Seiyaku Co Ltd | Thiazolopyrimidine derivative |
-
1983
- 1983-12-08 US US06/559,322 patent/US4522944A/en not_active Expired - Fee Related
- 1983-12-15 AT AT0438383A patent/AT385036B/de not_active IP Right Cessation
- 1983-12-15 GR GR73259A patent/GR79479B/el unknown
- 1983-12-16 NL NL8304340A patent/NL8304340A/nl not_active Application Discontinuation
- 1983-12-16 IT IT24207/83A patent/IT1194521B/it active
- 1983-12-19 AU AU22525/83A patent/AU558600B2/en not_active Ceased
- 1983-12-20 FI FI834698A patent/FI834698A7/fi not_active Application Discontinuation
- 1983-12-20 CH CH6783/83A patent/CH657136A5/de not_active IP Right Cessation
- 1983-12-21 DE DE19833346223 patent/DE3346223A1/de not_active Withdrawn
- 1983-12-22 IL IL70522A patent/IL70522A/xx not_active IP Right Cessation
- 1983-12-22 SU SU833682101A patent/SU1297731A3/ru active
- 1983-12-22 CA CA000444151A patent/CA1211440A/en not_active Expired
- 1983-12-22 DK DK593983A patent/DK593983A/da not_active Application Discontinuation
- 1983-12-22 SE SE8307133A patent/SE454698B/sv not_active IP Right Cessation
- 1983-12-23 FR FR8320704A patent/FR2538392B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2538392A1 (fr) | 1984-06-29 |
| IT1194521B (it) | 1988-09-22 |
| AT385036B (de) | 1988-02-10 |
| FI834698A0 (fi) | 1983-12-20 |
| SU1297731A3 (ru) | 1987-03-15 |
| IT8324207A0 (it) | 1983-12-16 |
| AU2252583A (en) | 1984-06-28 |
| FR2538392B1 (fr) | 1987-01-16 |
| GR79479B (cg-RX-API-DMAC7.html) | 1984-10-30 |
| AU558600B2 (en) | 1987-02-05 |
| DK593983D0 (da) | 1983-12-22 |
| US4522944A (en) | 1985-06-11 |
| FI834698A7 (fi) | 1984-06-24 |
| DK593983A (da) | 1984-06-24 |
| ATA438383A (de) | 1987-07-15 |
| IL70522A (en) | 1986-02-28 |
| CA1211440A (en) | 1986-09-16 |
| SE454698B (sv) | 1988-05-24 |
| DE3346223A1 (de) | 1984-06-28 |
| SE8307133L (sv) | 1984-06-24 |
| NL8304340A (nl) | 1984-07-16 |
| IL70522A0 (en) | 1984-03-30 |
| SE8307133D0 (sv) | 1983-12-22 |
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