NO116853B - - Google Patents
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- Publication number
- NO116853B NO116853B NO157264A NO15726465A NO116853B NO 116853 B NO116853 B NO 116853B NO 157264 A NO157264 A NO 157264A NO 15726465 A NO15726465 A NO 15726465A NO 116853 B NO116853 B NO 116853B
- Authority
- NO
- Norway
- Prior art keywords
- yield
- mol
- solid
- dark
- melting point
- Prior art date
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 33
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 10
- 235000019270 ammonium chloride Nutrition 0.000 claims description 9
- -1 azide salt Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000011968 lewis acid catalyst Substances 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 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 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000003776 cleavage reaction Methods 0.000 description 10
- 229910017053 inorganic salt Inorganic materials 0.000 description 10
- 230000007017 scission Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003536 tetrazoles Chemical class 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000007790 scraping Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- CIGSCDLAXLXDQV-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-(4-methylphenyl)sulfonylpiperazine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCN(C=2C=CC(F)=CC=2)CC1 CIGSCDLAXLXDQV-UHFFFAOYSA-N 0.000 description 1
- UUVXQOJRYRAKLO-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-4-phenylpiperazine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCN(C=2C=CC=CC=2)CC1 UUVXQOJRYRAKLO-UHFFFAOYSA-N 0.000 description 1
- CUTPTQNQXVVRDB-UHFFFAOYSA-N 1-phenylpiperazine;dihydrochloride Chemical compound Cl.Cl.C1CNCCN1C1=CC=CC=C1 CUTPTQNQXVVRDB-UHFFFAOYSA-N 0.000 description 1
- ONNCTSYEIOXVCV-UHFFFAOYSA-N 2-(4-phenylpiperazin-1-yl)acetonitrile Chemical compound C1CN(CC#N)CCN1C1=CC=CC=C1 ONNCTSYEIOXVCV-UHFFFAOYSA-N 0.000 description 1
- KTXUJUPSPCFJME-UHFFFAOYSA-N 3-(4-phenylpiperazin-1-yl)propanenitrile Chemical compound C1CN(CCC#N)CCN1C1=CC=CC=C1 KTXUJUPSPCFJME-UHFFFAOYSA-N 0.000 description 1
- BRVUCSKROBTQJE-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)piperazin-1-yl]propanenitrile Chemical compound C1=CC(F)=CC=C1N1CCN(CCC#N)CC1 BRVUCSKROBTQJE-UHFFFAOYSA-N 0.000 description 1
- CCMXPQPJYDDIJA-UHFFFAOYSA-N 4-(4-phenylpiperazin-1-yl)butanenitrile Chemical compound C1CN(CCCC#N)CCN1C1=CC=CC=C1 CCMXPQPJYDDIJA-UHFFFAOYSA-N 0.000 description 1
- BXRPHRDCYXUHDU-UHFFFAOYSA-N 4-[4-(3-chlorophenyl)piperazin-1-yl]butanenitrile Chemical compound ClC1=CC=CC(N2CCN(CCCC#N)CC2)=C1 BXRPHRDCYXUHDU-UHFFFAOYSA-N 0.000 description 1
- FKVCVFYHGNJBOB-UHFFFAOYSA-N Cl.Cl.FC1=CC=C(C=C1)N1CCN(CCC2=NN=NN2)CC1 Chemical compound Cl.Cl.FC1=CC=C(C=C1)N1CCN(CCC2=NN=NN2)CC1 FKVCVFYHGNJBOB-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229940045348 brown mixture Drugs 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- ANFZRGMDGDYNGA-UHFFFAOYSA-N ethyl acetate;propan-2-ol Chemical compound CC(C)O.CCOC(C)=O ANFZRGMDGDYNGA-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-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
- 239000000463 material Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 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
- XTTHMUYLNLEJRS-UHFFFAOYSA-N zolertine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCC=1N=NNN=1 XTTHMUYLNLEJRS-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US353273A US3231574A (en) | 1964-03-19 | 1964-03-19 | Piperazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116853B true NO116853B (pt) | 1969-06-02 |
Family
ID=23388423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO157264A NO116853B (pt) | 1964-03-19 | 1965-03-18 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3231574A (pt) |
| AT (1) | AT248429B (pt) |
| BE (1) | BE661396A (pt) |
| BR (1) | BR6567941D0 (pt) |
| CH (1) | CH471802A (pt) |
| DE (2) | DE1301820B (pt) |
| DK (1) | DK115406B (pt) |
| ES (1) | ES310663A1 (pt) |
| FR (1) | FR1559569A (pt) |
| GB (1) | GB1046302A (pt) |
| NL (2) | NL6503433A (pt) |
| NO (1) | NO116853B (pt) |
| SE (1) | SE308726B (pt) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3536715A (en) * | 1967-03-24 | 1970-10-27 | Miles Lab | 2-lower alkyl-5-(omega-(4-phenyl-1-piperazinyl) lower alkyl)-2h-tetrazoles |
| US3499900A (en) * | 1967-05-03 | 1970-03-10 | Miles Lab | Process for preparation of piperazyl alkyl derivatives of tetrazoles |
| DE2340716A1 (de) * | 1972-11-02 | 1975-02-20 | 8601 Steinfeld | Einrichtung zur elektronischen staubabscheidung |
| US4097479A (en) * | 1977-03-11 | 1978-06-27 | Miles Laboratories, Inc. | Synthesis of 5-substituted tetrazoles |
| EP4291191A1 (en) * | 2021-02-12 | 2023-12-20 | The Trustees Of Columbia University In The City Of New York | Novel compounds comprising a new class of transthyretin ligands for treatment of common age-related comorbidities |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2735852A (en) * | 1956-02-21 | N nxch | ||
| US2695295A (en) * | 1952-12-19 | 1954-11-23 | Mcneilab Inc | Unsymmetrical n, n'-substituted ethylenediamine and piperazine compounds |
| US2852515A (en) * | 1954-01-13 | 1958-09-16 | Sterling Drug Inc | Tertiary-aminoalkyl substituted tetrazoles and preparation thereof |
| US2987442A (en) * | 1959-02-17 | 1961-06-06 | Smith Kline French Lab | Method of treating hypertension with [2-(2, 6-dimethylphenoxy)-propyl]-trimethyl ammonium salts |
| US2997474A (en) * | 1959-10-12 | 1961-08-22 | Paul A J Janssen | 1-aryl-omega-(4-arylpiperazine) alkanols |
| US2986573A (en) * | 1961-01-18 | 1961-05-30 | Schering Corp | Method for the treatment of hypertension |
-
0
- NL NL125448D patent/NL125448C/xx active
- DE DENDAT1302810D patent/DE1302810B/de active Pending
-
1964
- 1964-03-19 US US353273A patent/US3231574A/en not_active Expired - Lifetime
-
1965
- 1965-03-08 GB GB9722/65A patent/GB1046302A/en not_active Expired
- 1965-03-16 FR FR1559569D patent/FR1559569A/fr not_active Expired
- 1965-03-17 CH CH375165A patent/CH471802A/de not_active IP Right Cessation
- 1965-03-17 ES ES0310663A patent/ES310663A1/es not_active Expired
- 1965-03-18 BR BR167941/65A patent/BR6567941D0/pt unknown
- 1965-03-18 SE SE3550/65A patent/SE308726B/xx unknown
- 1965-03-18 AT AT244865A patent/AT248429B/de active
- 1965-03-18 NL NL6503433A patent/NL6503433A/xx unknown
- 1965-03-18 NO NO157264A patent/NO116853B/no unknown
- 1965-03-19 BE BE661396D patent/BE661396A/xx unknown
- 1965-03-19 DK DK141865AA patent/DK115406B/da unknown
- 1965-03-19 DE DEM64591A patent/DE1301820B/de active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL6503433A (pt) | 1965-09-20 |
| BR6567941D0 (pt) | 1973-08-07 |
| DK115406B (da) | 1969-10-06 |
| AT248429B (de) | 1966-07-25 |
| SE308726B (pt) | 1969-02-24 |
| DE1301820B (de) | 1969-08-28 |
| NL125448C (pt) | |
| CH471802A (de) | 1969-04-30 |
| FR1559569A (pt) | 1969-03-14 |
| ES310663A1 (es) | 1966-01-01 |
| DE1302810B (pt) | |
| BE661396A (pt) | 1965-09-20 |
| US3231574A (en) | 1966-01-25 |
| GB1046302A (en) | 1966-10-19 |
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