US3011945A - Phenylcyclopropylamine -10-(omega-aminoalkyl)-phenothiazine ataractic composition - Google Patents
Phenylcyclopropylamine -10-(omega-aminoalkyl)-phenothiazine ataractic composition Download PDFInfo
- Publication number
- US3011945A US3011945A US12917A US1291760A US3011945A US 3011945 A US3011945 A US 3011945A US 12917 A US12917 A US 12917A US 1291760 A US1291760 A US 1291760A US 3011945 A US3011945 A US 3011945A
- Authority
- US
- United States
- Prior art keywords
- phenylcyclopropylamine
- phenothiazine
- ataractic
- aminoalkyl
- free base
- 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 - Lifetime
Links
- 230000002716 ataractic effect Effects 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 title description 22
- 229950000688 phenothiazine Drugs 0.000 title description 13
- AOTWIFLKURJQGE-UHFFFAOYSA-N n-cyclopropylaniline Chemical compound C1CC1NC1=CC=CC=C1 AOTWIFLKURJQGE-UHFFFAOYSA-N 0.000 title description 3
- 239000012458 free base Substances 0.000 claims description 13
- 231100000252 nontoxic Toxicity 0.000 claims description 12
- 230000003000 nontoxic effect Effects 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 description 17
- -1 dimethylamino, methylpiperazinyl Chemical group 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- AELCINSCMGFISI-UHFFFAOYSA-N 2-phenylcyclopropan-1-amine Chemical class NC1CC1C1=CC=CC=C1 AELCINSCMGFISI-UHFFFAOYSA-N 0.000 description 10
- 241000282414 Homo sapiens Species 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- 239000003937 drug carrier Substances 0.000 description 7
- 239000007903 gelatin capsule Substances 0.000 description 7
- 230000009471 action Effects 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- BTHVHSMCHJCPFU-OULXEKPRSA-N (1r,2s)-2-phenylcyclopropan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.N[C@@H]1C[C@H]1C1=CC=CC=C1 BTHVHSMCHJCPFU-OULXEKPRSA-N 0.000 description 5
- 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
- 239000008101 lactose Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000002990 phenothiazines Chemical class 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000000935 antidepressant agent Substances 0.000 description 4
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000994 depressogenic effect Effects 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000005469 granulation Methods 0.000 description 4
- 230000003179 granulation Effects 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BXDAOUXDMHXPDI-UHFFFAOYSA-N trifluoperazine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 BXDAOUXDMHXPDI-UHFFFAOYSA-N 0.000 description 4
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 3
- WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical compound [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000001430 anti-depressive effect Effects 0.000 description 3
- 229940005513 antidepressants Drugs 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
- 230000006872 improvement Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- SWOUGRBFXFILIB-UHFFFAOYSA-N 2-chloro-10-[3-(4-methylpiperazin-1-yl)propyl]phenothiazine;ethane-1,2-disulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O.C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 SWOUGRBFXFILIB-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 description 2
- ZGUGWUXLJSTTMA-UHFFFAOYSA-N Promazinum Chemical compound C1=CC=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZGUGWUXLJSTTMA-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000036524 ataraxia Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 229960000762 perphenazine Drugs 0.000 description 2
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000001433 sodium tartrate Substances 0.000 description 2
- 229960002167 sodium tartrate Drugs 0.000 description 2
- 235000011004 sodium tartrates Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 229940066767 systemic antihistamines phenothiazine derivative Drugs 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- AIUHRQHVWSUTGJ-UHFFFAOYSA-N thiopropazate Chemical compound C1CN(CCOC(=O)C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 AIUHRQHVWSUTGJ-UHFFFAOYSA-N 0.000 description 2
- 229960004728 thiopropazate Drugs 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- AELCINSCMGFISI-DTWKUNHWSA-N (1R,2S)-tranylcypromine Chemical compound N[C@@H]1C[C@H]1C1=CC=CC=C1 AELCINSCMGFISI-DTWKUNHWSA-N 0.000 description 1
- 125000004810 2-methylpropylene group Chemical group [H]C([H])([H])C([H])(C([H])([H])[*:2])C([H])([H])[*:1] 0.000 description 1
- BTHVHSMCHJCPFU-UHFFFAOYSA-N 2-phenylcyclopropan-1-amine;sulfuric acid Chemical compound OS(O)(=O)=O.NC1CC1C1=CC=CC=C1 BTHVHSMCHJCPFU-UHFFFAOYSA-N 0.000 description 1
- AKUVRZKNLXYTJX-UHFFFAOYSA-N 3-benzylazetidine Chemical compound C=1C=CC=CC=1CC1CNC1 AKUVRZKNLXYTJX-UHFFFAOYSA-N 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920001817 Agar Polymers 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 206010010144 Completed suicide Diseases 0.000 description 1
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 229940095672 calcium sulfate Drugs 0.000 description 1
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
- 229960001076 chlorpromazine Drugs 0.000 description 1
- 229960001657 chlorpromazine hydrochloride Drugs 0.000 description 1
- IAQRGUVFOMOMEM-ARJAWSKDSA-N cis-but-2-ene Chemical group C\C=C/C IAQRGUVFOMOMEM-ARJAWSKDSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000011950 custard Nutrition 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229940057307 dihydrate calcium sulfate Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 229960002690 fluphenazine Drugs 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 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
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 1
- AQMNNXSLDLIGII-UHFFFAOYSA-N n,n,2-trimethyl-3-(2-methylsulfanylphenothiazin-10-yl)propan-1-amine Chemical compound C1=CC=C2N(CC(C)CN(C)C)C3=CC(SC)=CC=C3SC2=C1 AQMNNXSLDLIGII-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 229950007538 pecazine Drugs 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- WIKYUJGCLQQFNW-UHFFFAOYSA-N prochlorperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 WIKYUJGCLQQFNW-UHFFFAOYSA-N 0.000 description 1
- 229960003111 prochlorperazine Drugs 0.000 description 1
- 229960003598 promazine Drugs 0.000 description 1
- 229960003910 promethazine Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 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
- 229960002324 trifluoperazine Drugs 0.000 description 1
- FTNWXGFYRHWUKG-UHFFFAOYSA-N triflupromazine hydrochloride Chemical compound [H+].[Cl-].C1=C(C(F)(F)F)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 FTNWXGFYRHWUKG-UHFFFAOYSA-N 0.000 description 1
- 229960004312 triflupromazine hydrochloride Drugs 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
Definitions
- a method of treating emotionally disturbed human beings in accordance with claim 10 characterized in that the trans-2-phenylcyclopropylamine sulfate and the 2- trifluoromethyl 10 [3 (1 methyl 4 piperazinyl) propyl]-phenothiazine dihydrochloride are combined with a pharmaceutical carrier.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12917A US3011945A (en) | 1960-03-07 | 1960-03-07 | Phenylcyclopropylamine -10-(omega-aminoalkyl)-phenothiazine ataractic composition |
| GB6764/61A GB911229A (en) | 1960-03-07 | 1961-02-23 | Improvements in or relating to ataractic compositions |
| BE600835A BE600835A (fr) | 1960-03-07 | 1961-03-02 | Compositions ataractiques. |
| FR854858A FR981M (es) | 1960-03-07 | 1961-03-07 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12917A US3011945A (en) | 1960-03-07 | 1960-03-07 | Phenylcyclopropylamine -10-(omega-aminoalkyl)-phenothiazine ataractic composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3011945A true US3011945A (en) | 1961-12-05 |
Family
ID=21757361
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12917A Expired - Lifetime US3011945A (en) | 1960-03-07 | 1960-03-07 | Phenylcyclopropylamine -10-(omega-aminoalkyl)-phenothiazine ataractic composition |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3011945A (es) |
| BE (1) | BE600835A (es) |
| FR (1) | FR981M (es) |
| GB (1) | GB911229A (es) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3134676A (en) * | 1961-06-21 | 1964-05-26 | Smith Kline French Lab | Animal feed compositions and methods for their administration |
| US3177255A (en) * | 1961-01-07 | 1965-04-06 | Hoechst Ag | Phenylpropylamine derivatives |
| US3188347A (en) * | 1961-12-18 | 1965-06-08 | Schering Corp | 5(4-dimethylaminocyclohexy)-dibenzo [a, d] cyclohepta[1, 4]diene and salts thereof |
| US3192207A (en) * | 1963-03-11 | 1965-06-29 | Robins Co Inc A H | Aminoalkyl esters of 4-carboxyalkyl-2-pyrrolidinones and 4-carboxyalkyl-2-thionpyrrolidinones |
| US3192229A (en) * | 1962-07-03 | 1965-06-29 | Colgate Palmolive Co | Phenylcyclopropyl amides |
| US3221054A (en) * | 1962-01-04 | 1965-11-30 | May & Baker Ltd | N-propargyl-phenoxyalkylamines |
| US3515785A (en) * | 1958-12-06 | 1970-06-02 | Geigy Chem Corp | Compositions and methods for treating endogenous depression with 3-chloro - 5 - (gamma - dimethylamino - propyl)-iminodibenzyl |
| US3621097A (en) * | 1970-03-30 | 1971-11-16 | Jan Marcel Didier Aron Samuel | Method and compositions for treatment of mental illness |
| WO2016210292A1 (en) | 2015-06-25 | 2016-12-29 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion, enrichment, and maintenance |
| WO2017161001A1 (en) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4444789A (en) * | 1980-05-30 | 1984-04-24 | University Of Georgia Research Foundation, Inc. | Use of 8-anilino-1-naphthalenesulfonate as a vaginal contraceptive |
-
1960
- 1960-03-07 US US12917A patent/US3011945A/en not_active Expired - Lifetime
-
1961
- 1961-02-23 GB GB6764/61A patent/GB911229A/en not_active Expired
- 1961-03-02 BE BE600835A patent/BE600835A/fr unknown
- 1961-03-07 FR FR854858A patent/FR981M/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| None * |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3515785A (en) * | 1958-12-06 | 1970-06-02 | Geigy Chem Corp | Compositions and methods for treating endogenous depression with 3-chloro - 5 - (gamma - dimethylamino - propyl)-iminodibenzyl |
| US3177255A (en) * | 1961-01-07 | 1965-04-06 | Hoechst Ag | Phenylpropylamine derivatives |
| US3134676A (en) * | 1961-06-21 | 1964-05-26 | Smith Kline French Lab | Animal feed compositions and methods for their administration |
| US3188347A (en) * | 1961-12-18 | 1965-06-08 | Schering Corp | 5(4-dimethylaminocyclohexy)-dibenzo [a, d] cyclohepta[1, 4]diene and salts thereof |
| US3221054A (en) * | 1962-01-04 | 1965-11-30 | May & Baker Ltd | N-propargyl-phenoxyalkylamines |
| US3192229A (en) * | 1962-07-03 | 1965-06-29 | Colgate Palmolive Co | Phenylcyclopropyl amides |
| US3192207A (en) * | 1963-03-11 | 1965-06-29 | Robins Co Inc A H | Aminoalkyl esters of 4-carboxyalkyl-2-pyrrolidinones and 4-carboxyalkyl-2-thionpyrrolidinones |
| US3621097A (en) * | 1970-03-30 | 1971-11-16 | Jan Marcel Didier Aron Samuel | Method and compositions for treatment of mental illness |
| WO2016210292A1 (en) | 2015-06-25 | 2016-12-29 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion, enrichment, and maintenance |
| WO2017161001A1 (en) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| EP4049665A1 (en) | 2016-03-15 | 2022-08-31 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
Also Published As
| Publication number | Publication date |
|---|---|
| BE600835A (fr) | 1961-09-04 |
| FR981M (es) | 1961-12-04 |
| GB911229A (en) | 1962-11-21 |
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