CH516513A - Verfahren zur Herstellung von Aminderivaten - Google Patents

Verfahren zur Herstellung von Aminderivaten

Info

Publication number: CH516513A
Authority: CH; Switzerland
Prior art keywords: propanol; acid; radical; isopropylamino; parts
Prior art date: 1967-07-24

Application number

CH1108268A

Other languages

German (de)

English (en)

Inventor

Leigh Thomas

Original Assignee

Ici Ltd

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.)

1967-07-24

Filing date

1968-07-24

Publication date

1971-12-15

1968-07-24 Application filed by Ici Ltd filed Critical Ici Ltd

1971-12-15 Publication of CH516513A publication Critical patent/CH516513A/de

Links

239000002876 beta blocker Substances 0.000 title abstract 3
229940030611 beta-adrenergic blocking agent Drugs 0.000 title abstract 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title description 6
229960004592 isopropanol Drugs 0.000 title description 5
125000003282 alkyl amino group Chemical group 0.000 title 1
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
-1 1-methyloctyl Chemical group 0.000 claims description 51
238000000034 method Methods 0.000 claims description 30
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 24
MBHQWSSJIBMVIA-UHFFFAOYSA-N 1-(4-aminophenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(N)C=C1 MBHQWSSJIBMVIA-UHFFFAOYSA-N 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
239000003795 chemical substances by application Substances 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 9
150000008065 acid anhydrides Chemical class 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 5
125000003435 aroyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
YKTJALYPSUHBEX-UHFFFAOYSA-N n-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]benzamide Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1NC(=O)C1=CC=CC=C1 YKTJALYPSUHBEX-UHFFFAOYSA-N 0.000 claims description 5
IZBZNVKZOMVCIF-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC)O)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC)O)C=C1 IZBZNVKZOMVCIF-UHFFFAOYSA-N 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000002576 ketones Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
ZGKSAQBKNAFPSP-UHFFFAOYSA-N C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC2CCCC2)O)C=C1 Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC2CCCC2)O)C=C1 ZGKSAQBKNAFPSP-UHFFFAOYSA-N 0.000 claims description 3
125000001589 carboacyl group Chemical group 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
BPENFEPYBVXUII-UHFFFAOYSA-N n-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanamide Chemical compound CCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C=C1 BPENFEPYBVXUII-UHFFFAOYSA-N 0.000 claims description 3
PCYQHVPDZYOFAK-UHFFFAOYSA-N n-[4-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]acetamide Chemical compound CC(=O)NC1=CC=C(OCC(O)CNC(C)(C)C)C=C1 PCYQHVPDZYOFAK-UHFFFAOYSA-N 0.000 claims description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
239000005711 Benzoic acid Substances 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims description 2
235000010233 benzoic acid Nutrition 0.000 claims description 2
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
150000001718 carbodiimides Chemical class 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
239000000047 product Substances 0.000 claims description 2
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
235000011054 acetic acid Nutrition 0.000 claims 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
125000005336 allyloxy group Chemical group 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
235000015165 citric acid Nutrition 0.000 claims 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
239000004310 lactic acid Substances 0.000 claims 1
235000014655 lactic acid Nutrition 0.000 claims 1
235000006408 oxalic acid Nutrition 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
235000002906 tartaric acid Nutrition 0.000 claims 1
230000010933 acylation Effects 0.000 abstract description 3
238000005917 acylation reaction Methods 0.000 abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
239000000203 mixture Substances 0.000 description 44
239000000243 solution Substances 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 10
DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
239000007787 solid Substances 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CHZBWWONDNZRCC-UHFFFAOYSA-N Cl.C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC(C)C)O)C=C1 Chemical compound Cl.C(C1=CC=CC=C1)(=O)NC1=CC=C(OCC(CNC(C)C)O)C=C1 CHZBWWONDNZRCC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
GOVABHXGXSQUGN-UHFFFAOYSA-N N-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]ethanesulfonamide Chemical compound C(C)S(=O)(=O)NC1=CC=C(OCC(CNC(C)C)O)C=C1 GOVABHXGXSQUGN-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002024 ethyl acetate extract Substances 0.000 description 3
239000000284 extract Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000012265 solid product Substances 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
YBADLXQNJCMBKR-UHFFFAOYSA-M (4-nitrophenyl)acetate Chemical compound [O-]C(=O)CC1=CC=C([N+]([O-])=O)C=C1 YBADLXQNJCMBKR-UHFFFAOYSA-M 0.000 description 1
RPMSSDLRPDBMIM-UHFFFAOYSA-N 1-(4-aminophenoxy)-3-(cyclopentylamino)propan-2-ol Chemical compound C1=CC(N)=CC=C1OCC(O)CNC1CCCC1 RPMSSDLRPDBMIM-UHFFFAOYSA-N 0.000 description 1
HTPZDOJSYDALAA-UHFFFAOYSA-N 1-(4-aminophenoxy)-3-(methylamino)propan-2-ol Chemical compound CNCC(O)COC1=CC=C(N)C=C1 HTPZDOJSYDALAA-UHFFFAOYSA-N 0.000 description 1
IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
GQMVLTOPXFKQIC-UHFFFAOYSA-N N-[3-ethoxy-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=CC(=C(OCC(CNC(C)C)O)C=C1)OCC GQMVLTOPXFKQIC-UHFFFAOYSA-N 0.000 description 1
IJZAZTQFZPEGOB-UHFFFAOYSA-N N-[3-ethoxy-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]propanamide Chemical compound C(C)OC1=C(OCC(CNC(C)C)O)C=CC(=C1)NC(CC)=O IJZAZTQFZPEGOB-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
BQOWUDKEXDCGQS-UHFFFAOYSA-N [CH]1CCCC1 Chemical compound [CH]1CCCC1 BQOWUDKEXDCGQS-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000009835 boiling Methods 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
150000001860 citric acid derivatives Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000011282 treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1108268A 1967-07-24 1968-07-24 Verfahren zur Herstellung von Aminderivaten CH516513A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3397367A GB1185046A (en)	1967-07-24	1967-07-24	Process for the Manufacture of Amine Derivatives

Publications (1)

Publication Number	Publication Date
CH516513A true CH516513A (de)	1971-12-15

Family

ID=10359759

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1108268A CH516513A (de)	1967-07-24	1968-07-24	Verfahren zur Herstellung von Aminderivaten

Country Status (9)

Country	Link
AT (1)	AT286263B (cs)
CA (1)	CA931582A (cs)
CH (1)	CH516513A (cs)
CS (1)	CS158622B2 (cs)
ES (1)	ES356456A2 (cs)
GB (1)	GB1185046A (cs)
PL (1)	PL72566B1 (cs)
SE (1)	SE357360B (cs)
SU (1)	SU375842A3 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4852730A (cs) *	1971-11-02	1973-07-24
DE2948056A1 (de) *	1979-11-29	1981-06-04	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue aminopropanolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1967
- 1967-07-24 GB GB3397367A patent/GB1185046A/en not_active Expired
1968
- 1968-07-19 CS CS529368A patent/CS158622B2/cs unknown
- 1968-07-23 SU SU1260041A patent/SU375842A3/ru active
- 1968-07-23 SE SE1003068A patent/SE357360B/xx unknown
- 1968-07-23 PL PL12827968A patent/PL72566B1/pl unknown
- 1968-07-24 ES ES356456A patent/ES356456A2/es not_active Expired
- 1968-07-24 CH CH1108268A patent/CH516513A/de not_active IP Right Cessation
- 1968-07-24 AT AT719068A patent/AT286263B/de not_active IP Right Cessation
- 1968-07-24 CA CA025891A patent/CA931582A/en not_active Expired

Also Published As

Publication number	Publication date
CA931582A (en)	1973-08-07
SE357360B (cs)	1973-06-25
AT286263B (de)	1970-12-10
GB1185046A (en)	1970-03-18
ES356456A2 (es)	1970-04-01
PL72566B1 (cs)	1974-08-30
SU375842A3 (cs)	1973-03-23
CS158622B2 (cs)	1974-11-25

Legal Events

Date	Code	Title	Description
1977-02-28	PL	Patent ceased

Publication	Publication Date	Title
DE3013162A1 (de)	1980-10-30	N-substituierte tetrahydrophthalimide und herbizide mittel mit einem gehalt derselben
DE1620035A1 (de)	1970-02-12	3-Amino-5-X-6-halogenpyrazinonitrile und Verfahren zu deren Herstellung
DE3688004T2 (de)	1993-06-24	Verfahren zur herstellung herbizider 2-(4,4-disubstituierter-5-oxo-2-imidazolin-2yl)benzoesaeuren, -nicotinsaeuren und chinolin-3-carbonsaeuren, ester und salze.
DE69916512T2 (de)	2004-08-19	Fluor enthaltende Anilin-Verbindungen
CH626351A5 (cs)	1981-11-13
CH516513A (de)	1971-12-15	Verfahren zur Herstellung von Aminderivaten
DE3702964A1 (de)	1988-08-11	Aryloxycarbonsaeurederivate, ihre herstellung und verwendung
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
CH522651A (de)	1972-05-15	Verfahren zur Herstellung von Nitroimidazolcarbamaten bzw.-thiocarbamaten
DE3629441A1 (de)	1988-03-03	Neue phenoxycarbonsaeurederivate, ihre herstellung und verwendung
CH529766A (de)	1972-10-31	Verfahren zur Herstellung von Aryloxy-isoalkyl- 2-imidazolinen
EP0539330B1 (de)	1995-05-17	Verfahren zur Herstellung substituierter Indole
AT250338B (de)	1966-11-10	Verfahren zur Herstellung neuer, basischer Derivate von substituierten Benzofuran-2-carbonsäuren und deren Salzen
DE1670143C3 (cs)	1974-05-30
DD151447A1 (de)	1981-10-21	Verfahren zur herstellung von amidinen und deren salzen
AT214923B (de)	1961-05-10	Verfahren zur Herstellung von neuen Piperazinderivaten
DE2619165A1 (de)	1977-11-17	Indazolderivate und verfahren zu ihrer herstellung
DE2345651A1 (de)	1974-03-28	Indolylalkylamine und verfahren zu ihrer herstellung
AT289831B (de)	1971-05-10	Verfahren zur Herstellung von neuen substituierten Phenylcarbaminsäureestern von zyklischen Aminoalkoholen und ihren optischen Isomeren sowie ihrer Säureadditionssalze
AT388912B (de)	1989-09-25	Verfahren zur herstellung von alkylendiaminen und ihren salzen
DE2212693A1 (de)	1972-10-05	Dihydro-2-aminoisochinoline und Verfahren zu deren Herstellung
AT368488B (de)	1982-10-11	Verfahren zur herstellung von 2-substituierten 1-(2,6-dimethylphenoxy)-propanen
EP0090769A2 (de)	1983-10-05	Verfahren zur Herstellung von 1,2,5,6-Tetrahydro-4H-pyrrolo(3,2,1-ij)-chinolin-4-on und neue 5-Halogen-1,2,3-(1,2-dihydropyrrolo)-4-chinolone als Zwischenprodukte zur Durchführung des Verfahrens
DE2041734A1 (de)	1972-02-24	Carbamate der 2-Phenylhydrazino-2-imidazoline,Verfahren zu ihrer Herstellung und ihre Verwendung als Ektoparasitizide
AT401931B (de)	1996-12-27	Verfahren zur herstellung von (s,s)-(n-(1- ethoxycarbonyl-3-oxo-3-phenylpropyl)-alanin)- (phenylmethyl)ester