CH616401A5 - - Google Patents

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Info

Publication number: CH616401A5
Authority: CH; Switzerland
Prior art keywords: formula; compounds; hydrogen; methyl; prepared
Prior art date: 1974-04-27

Application number

CH176579A

Other languages

German (de)

English (en)

Inventor

Kurt Dr Schromm

Anton Dr Mentrup

Ernst Otto Dr Renth

Ludwig Dr Pichler

Werner Dr Traunecker

Original Assignee

Boehringer Sohn Ingelheim

Priority date (The priority date 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 date listed.)

1974-04-27

Filing date

1979-02-22

Publication date

1980-03-31

1979-02-22 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1980-03-31 Publication of CH616401A5 publication Critical patent/CH616401A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 18
238000000034 method Methods 0.000 claims description 15
239000003054 catalyst Substances 0.000 claims description 11
-1 methoxy, ethoxy, methylthio Chemical group 0.000 claims description 9
239000007868 Raney catalyst Substances 0.000 claims description 7
229910000564 Raney nickel Inorganic materials 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 5
230000003287 optical effect Effects 0.000 claims description 5
239000007858 starting material Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
150000002431 hydrogen Chemical class 0.000 claims 3
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 2
239000002585 base Substances 0.000 claims 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
150000004678 hydrides Chemical class 0.000 claims 2
150000002576 ketones Chemical class 0.000 claims 2
229910052763 palladium Inorganic materials 0.000 claims 2
229910052697 platinum Inorganic materials 0.000 claims 2
239000012279 sodium borohydride Substances 0.000 claims 2
229910000033 sodium borohydride Inorganic materials 0.000 claims 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
239000002262 Schiff base Substances 0.000 claims 1
150000004753 Schiff bases Chemical class 0.000 claims 1
238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
239000002904 solvent Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000011976 maleic acid Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
239000000203 mixture Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 description 2
WUKHOVCMWXMOOA-UHFFFAOYSA-N 2-(3-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC([N+]([O-])=O)=C1 WUKHOVCMWXMOOA-UHFFFAOYSA-N 0.000 description 2
WAVKEPUFQMUGBP-UHFFFAOYSA-N 2-(3-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=CC(CC#N)=C1 WAVKEPUFQMUGBP-UHFFFAOYSA-N 0.000 description 2
ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
CWNPOQFCIIFQDM-UHFFFAOYSA-N 3-nitrobenzyl alcohol Chemical compound OCC1=CC=CC([N+]([O-])=O)=C1 CWNPOQFCIIFQDM-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
230000005923 long-lasting effect Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
ZEGYACPSDGNOIE-UHFFFAOYSA-N n-[3-(2-aminopropyl)phenyl]acetamide;hydrochloride Chemical compound Cl.CC(N)CC1=CC=CC(NC(C)=O)=C1 ZEGYACPSDGNOIE-UHFFFAOYSA-N 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000001975 sympathomimetic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
BZXSPJGWGWTMPY-UHFFFAOYSA-N 1-[3-(2-aminopropyl)phenyl]-3-methylurea Chemical compound CNC(=O)NC1=CC=CC(CC(C)N)=C1 BZXSPJGWGWTMPY-UHFFFAOYSA-N 0.000 description 1
SZSWEYKUELOAGN-UHFFFAOYSA-N 3-(2-aminopropyl)aniline Chemical compound CC(N)CC1=CC=CC(N)=C1 SZSWEYKUELOAGN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
RPEAGHGKWIVGCO-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.CN(S(=O)(=O)NC=1C=C(C=CC1)CC(C)N)C Chemical compound C(C=C/C(=O)O)(=O)O.CN(S(=O)(=O)NC=1C=C(C=CC1)CC(C)N)C RPEAGHGKWIVGCO-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
FAUNUFBYLAIBPQ-UHFFFAOYSA-N Cl.C(C)C(=S)NC=1C=C(C=CC1)CC(C)N Chemical compound Cl.C(C)C(=S)NC=1C=C(C=CC1)CC(C)N FAUNUFBYLAIBPQ-UHFFFAOYSA-N 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
XBVDMKTYZIBTOH-UHFFFAOYSA-N N-[3-[2-(ethylamino)ethyl]phenyl]acetamide hydrochloride Chemical compound Cl.CCNCCC1=CC=CC(NC(C)=O)=C1 XBVDMKTYZIBTOH-UHFFFAOYSA-N 0.000 description 1
UGWRUWRFVMTRNO-UHFFFAOYSA-N N-[3-[2-(methylamino)propyl]phenyl]acetamide hydrochloride Chemical compound Cl.CNC(C)CC1=CC=CC(NC(C)=O)=C1 UGWRUWRFVMTRNO-UHFFFAOYSA-N 0.000 description 1
206010062119 Sympathomimetic effect Diseases 0.000 description 1
PLOVNJWUKBMEJQ-UHFFFAOYSA-N [3-(2-aminopropyl)phenyl]urea Chemical compound CC(N)CC1=CC=CC(NC(N)=O)=C1 PLOVNJWUKBMEJQ-UHFFFAOYSA-N 0.000 description 1
ATFVEZSSZDYHBL-UHFFFAOYSA-N [chlorosulfonyloxy(methyl)amino]methane Chemical compound CN(C)OS(Cl)(=O)=O ATFVEZSSZDYHBL-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
229940015607 hydro 40 Drugs 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
125000006626 methoxycarbonylamino group Chemical group 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
CRJNAOPRMRTKFU-UHFFFAOYSA-N n-[3-(2-aminopropyl)phenyl]formamide;hydrochloride Chemical compound Cl.CC(N)CC1=CC=CC(NC=O)=C1 CRJNAOPRMRTKFU-UHFFFAOYSA-N 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH176579A 1974-04-27 1979-02-22 CH616401A5 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2420618A DE2420618C2 (de)	1974-04-27	1974-04-27	Aminoalkylanilide, Verfahren zu ihrer Herstellung sowie pharmazeutische Zubereitungen, die diese Aminoalkylanilide enthalten

Publications (1)

Publication Number	Publication Date
CH616401A5 true CH616401A5 (fr)	1980-03-31

Family

ID=5914207

Family Applications (3)

Application Number	Title	Priority Date
CH530375A CH614697A5 (fr)	1974-04-27	1975-04-25
CH176579A CH616401A5 (fr)	1974-04-27	1979-02-22
CH176679A CH616146A5 (fr)	1974-04-27	1979-02-22

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CH530375A CH614697A5 (fr)	1974-04-27	1975-04-25

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH176679A CH616146A5 (fr)	1974-04-27	1979-02-22

Country Status (27)

Country	Link
US (1)	US4015011A (fr)
JP (1)	JPS5828269B2 (fr)
AT (1)	AT350529B (fr)
BE (1)	BE828430A (fr)
BG (2)	BG26372A4 (fr)
CA (1)	CA1061357A (fr)
CH (3)	CH614697A5 (fr)
CS (2)	CS216828B2 (fr)
DD (1)	DD122374A5 (fr)
DE (1)	DE2420618C2 (fr)
DK (1)	DK180675A (fr)
ES (7)	ES437032A1 (fr)
FI (1)	FI63931C (fr)
FR (1)	FR2268520B1 (fr)
GB (1)	GB1501436A (fr)
HU (1)	HU172615B (fr)
IE (1)	IE42119B1 (fr)
IL (1)	IL47170A (fr)
NL (1)	NL7504917A (fr)
NO (1)	NO141207C (fr)
PH (2)	PH11982A (fr)
PL (2)	PL96308B1 (fr)
RO (2)	RO81766A (fr)
SE (2)	SE411205B (fr)
SU (2)	SU555843A3 (fr)
YU (1)	YU105275A (fr)
ZA (1)	ZA752685B (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4163060A (en) *	1974-04-08	1979-07-31	U.S. Philips Corporation	Aralkylamino carboxylic acids and derivatives having spasmolytic activity
US4146645A (en) *	1974-04-27	1979-03-27	Boehringer Ingelheim Gmbh	Hypertensive phenylalkylamines and salts thereof
US4145363A (en) *	1975-02-05	1979-03-20	Yamanouchi Pharmaceutical Co., Ltd.	4-Carbamoylamino-α-aminomethylbenzyl alcohol derivatives
US4088785A (en) *	1976-03-25	1978-05-09	William H. Rorer, Inc.	Amidinoureas for the treatment of cardinascular disorders
US4754047A (en) *	1979-08-16	1988-06-28	American Cyanamid Company	Phenylethanolamine derivatives and acid addition salts thereof for enhancing the growth rate of meat-producing animals and/or improving the efficiency of feed utilization thereby
US4477470A (en) *	1983-10-20	1984-10-16	Smithkline Beckman Corporation	Method for producing diuresis using m-amino-α-methylphenethylamine
JPS6155683U (fr) *	1984-09-17	1986-04-14
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1974
- 1974-04-27 DE DE2420618A patent/DE2420618C2/de not_active Expired
1975
- 1975-04-02 AT AT247875A patent/AT350529B/de not_active IP Right Cessation
- 1975-04-22 FI FI751199A patent/FI63931C/fi not_active IP Right Cessation
- 1975-04-24 YU YU01052/75A patent/YU105275A/xx unknown
- 1975-04-24 DK DK180675A patent/DK180675A/da not_active Application Discontinuation
- 1975-04-25 BG BG030690A patent/BG26372A4/xx unknown
- 1975-04-25 NL NL7504917A patent/NL7504917A/xx not_active Application Discontinuation
- 1975-04-25 JP JP50050607A patent/JPS5828269B2/ja not_active Expired
- 1975-04-25 SE SE7504858A patent/SE411205B/xx unknown
- 1975-04-25 IE IE936/75A patent/IE42119B1/en unknown
- 1975-04-25 RO RO7586026A patent/RO81766A/fr unknown
- 1975-04-25 CS CS756837A patent/CS216828B2/cs unknown
- 1975-04-25 PL PL1975193923A patent/PL96308B1/pl unknown
- 1975-04-25 BG BG029781A patent/BG27738A3/xx unknown
- 1975-04-25 FR FR7513097A patent/FR2268520B1/fr not_active Expired
- 1975-04-25 HU HU75BO00001554A patent/HU172615B/hu unknown
- 1975-04-25 CH CH530375A patent/CH614697A5/xx not_active IP Right Cessation
- 1975-04-25 NO NO751491A patent/NO141207C/no unknown
- 1975-04-25 CA CA225,445A patent/CA1061357A/fr not_active Expired
- 1975-04-25 RO RO7582093A patent/RO70894A/fr unknown
- 1975-04-25 ZA ZA00752685A patent/ZA752685B/xx unknown
- 1975-04-25 DD DD185702A patent/DD122374A5/xx unknown
- 1975-04-25 US US05/571,719 patent/US4015011A/en not_active Expired - Lifetime
- 1975-04-25 PL PL1975179934A patent/PL96224B1/pl unknown
- 1975-04-25 IL IL47170A patent/IL47170A/xx unknown
- 1975-04-25 SU SU2128340A patent/SU555843A3/ru active
- 1975-04-25 CS CS752917A patent/CS216827B2/cs unknown
- 1975-04-25 BE BE155812A patent/BE828430A/fr not_active IP Right Cessation
- 1975-04-25 GB GB17328/75A patent/GB1501436A/en not_active Expired
- 1975-04-26 ES ES437032A patent/ES437032A1/es not_active Expired
- 1975-04-28 PH PH17108A patent/PH11982A/en unknown
1976
- 1976-06-10 SU SU762370950A patent/SU606549A3/ru active
- 1976-10-19 ES ES452514A patent/ES452514A1/es not_active Expired
- 1976-10-19 ES ES452511A patent/ES452511A1/es not_active Expired
- 1976-10-19 ES ES452515A patent/ES452515A1/es not_active Expired
- 1976-10-19 ES ES452510A patent/ES452510A1/es not_active Expired
- 1976-10-19 ES ES452513A patent/ES452513A1/es not_active Expired
- 1976-10-19 ES ES452512A patent/ES452512A1/es not_active Expired
1977
- 1977-11-24 PH PH20480A patent/PH14732A/en unknown
1978
- 1978-09-26 SE SE7810002A patent/SE7810002L/xx unknown
1979
- 1979-02-22 CH CH176579A patent/CH616401A5/de not_active IP Right Cessation
- 1979-02-22 CH CH176679A patent/CH616146A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
IE42119B1 (en)	1980-06-04
BE828430A (fr)	1975-10-27
BG26372A4 (bg)	1979-03-15
CH614697A5 (fr)	1979-12-14
HU172615B (hu)	1978-11-28
IL47170A0 (en)	1975-06-25
ES437032A1 (es)	1977-04-16
RO70894A (fr)	1982-02-26
BG27738A3 (en)	1979-12-12
US4015011A (en)	1977-03-29
AU8051075A (en)	1976-10-28
SU555843A3 (ru)	1977-04-25
JPS50149630A (fr)	1975-11-29
NO141207C (no)	1980-01-30
JPS5828269B2 (ja)	1983-06-15
ATA247875A (de)	1978-11-15
ZA752685B (en)	1976-12-29
ES452512A1 (es)	1977-11-01
SE7504858L (sv)	1975-10-28
ES452511A1 (es)	1977-11-01
YU105275A (en)	1982-02-28
PH14732A (en)	1981-11-19
RO81766B (ro)	1983-05-30
FI751199A (fr)	1975-10-28
NO751491L (fr)	1975-10-28
ES452510A1 (es)	1977-11-01
ES452513A1 (es)	1977-11-01
PL96308B1 (pl)	1977-12-31
DD122374A5 (fr)	1976-10-05
NL7504917A (nl)	1975-10-29
DE2420618A1 (de)	1975-11-13
CA1061357A (fr)	1979-08-28
IL47170A (en)	1980-07-31
GB1501436A (en)	1978-02-15
SU606549A3 (ru)	1978-05-05
CS216827B2 (en)	1982-11-26
CS216828B2 (en)	1982-11-26
DK180675A (da)	1975-10-28
DE2420618C2 (de)	1982-09-16
IE42119L (en)	1975-10-27
RO81766A (fr)	1983-06-01
ES452514A1 (es)	1977-11-01
ES452515A1 (es)	1977-11-01
FI63931B (fi)	1983-05-31
FR2268520B1 (fr)	1982-02-12
PL96224B1 (pl)	1977-12-31
PH11982A (en)	1978-10-04
CH616146A5 (fr)	1980-03-14
SE7810002L (sv)	1978-09-22
SE411205B (sv)	1979-12-10
NO141207B (no)	1979-10-22
FI63931C (fi)	1983-09-12
FR2268520A1 (fr)	1975-11-21
AT350529B (de)	1979-06-11

Publication	Publication Date	Title
EP0753506B1 (fr)	1999-08-18	Composés 6-diméthylaminométhyl-1-phényl-cyclohexane comme agents pharmaceutiques
CH616401A5 (fr)	1980-03-31
DE2434911C2 (de)	1984-11-29	Phenyläthylamin-Derivate und pharmazeutische Zusammensetzungen
US4029731A (en)	1977-06-14	Aminophenyltetralin compounds
US4045488A (en)	1977-08-30	Aminophenyltetralin compounds
DE2413102B2 (de)	1980-01-17	Verfahren zur Herstellung von t-(33-Dihydroxyphenyl)-)-hydroxy-2- eckige Klammer auf l-methyl-2-(4-hydroxyphenyl)- äthyl] -aminoäthan
DE2418030A1 (de)	1974-11-07	Amine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2951247C2 (fr)	1988-03-10
US4272533A (en)	1981-06-09	N-Phenylindoline derivatives, and pharmaceutical compositions containing them
EP0082461B1 (fr)	1987-03-04	Phénoxyalcanolamines et phénoxyalcanol-cycloalcoylamines substituées, procédé pour leur préparation, compositions pharmaceutiques contenant ces composés et intermédiaires
EP0065295A1 (fr)	1982-11-24	Dérivés de la tryptamine et de la thiényloxypropanolamine, procédé pour leur préparation, compositions pharmaceutiques les contenant et préparation de celles-ci
US4467094A (en)	1984-08-21	Precursors to ethylenediamine derivatives
DE2458908A1 (de)	1975-09-11	Alkanolaminderivate
DE2225332A1 (de)	1972-12-14	1 eckige Klammer auf 4 Hydroxy 3 (hydroxymethyl) phenyl eckige Klammer zu 1 hydroxy 2 aralkylaminoathane
DE3888811T2 (de)	1994-09-29	Tricyclische Carbamate, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung.
CH636858A5 (de)	1983-06-30	Verfahren zur herstellung neuer phenylazacycloalkane.
AT359999B (de)	1980-12-10	Verfahren zur herstellung von neuen amino- phenylalkylaminen
DE69210629T2 (de)	1996-09-19	5-aminosulfonanilid-verbindungen
DE2320058A1 (de)	1973-11-08	Neue propylen-diamin-derivate und verfahren zur herstellung derselben
Sunko et al.	1953	Studies in the Sphingolipids Series. II. Synthesis of Enantiomeric Sphingines
US3423415A (en)	1969-01-21	4 - (n - (3,3 - diphenyl - propyl) - amino) - 1-methyl-3-phenyl-piperidine and intermediates thereto
DE19718334A1 (de)	1998-11-05	Neue Benzylaminderivate und Phenylethylaminderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
Kralt et al.	1958	Ionylamines I: Synthesis of di‐and tetra‐hydro‐α‐and‐β‐ionylamines and their spasmolytic action
CH621782A5 (fr)	1981-02-27
CH556323A (de)	1974-11-29	Verfahren zur herstellung von neuen naphthylalkylaminen.

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Date	Code	Title	Description
1984-12-28	PL	Patent ceased
2024-10-31	PL	Patent ceased