CA1041545A - Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines - Google Patents

Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines

Info

Publication number: CA1041545A
Authority: CA; Canada
Prior art keywords: amino; process according; effected; compound; prepared
Prior art date: 1973-11-02
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

Application number

CA212,850A

Other languages

English (en)

French (fr)

Other versions

CA212850S (en

Inventor

Johannes Keck

Gerd Kruger

Helmut Pieper

Klaus-Reinhold Noll

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Original Assignee

Dr Karl Thomae GmbH

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.)

1973-11-02

Filing date

1974-11-01

Publication date

1978-10-31

1974-11-01 Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH

1978-10-31 Application granted granted Critical

1978-10-31 Publication of CA1041545A publication Critical patent/CA1041545A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 29
238000002360 preparation method Methods 0.000 title claims abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 24
239000002253 acid Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 9
238000006243 chemical reaction Methods 0.000 claims abstract 6
229910000033 sodium borohydride Inorganic materials 0.000 claims description 9
239000012279 sodium borohydride Substances 0.000 claims description 9
SAFBWLLTIPIZTP-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-2-oxoacetaldehyde;hydrate Chemical compound O.NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl SAFBWLLTIPIZTP-UHFFFAOYSA-N 0.000 claims description 8
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
JLPKZJDZXIKSCP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=C(N)C(Cl)=C1 JLPKZJDZXIKSCP-UHFFFAOYSA-N 0.000 claims description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 3
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052987 metal hydride Inorganic materials 0.000 claims description 3
150000004681 metal hydrides Chemical class 0.000 claims description 3
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims description 2
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims 2
OPAPFFIFYJTRRI-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclobutylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC1CCC1)O)Cl OPAPFFIFYJTRRI-UHFFFAOYSA-N 0.000 claims 1
GSTCQRQIQKYHLZ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclopentylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC1CCCC1)O)Cl GSTCQRQIQKYHLZ-UHFFFAOYSA-N 0.000 claims 1
FRLAHIZRTFRSMT-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(cyclopropylamino)ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CNC1CC1 FRLAHIZRTFRSMT-UHFFFAOYSA-N 0.000 claims 1
STJMRWALKKWQGH-UHFFFAOYSA-N clenbuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(Cl)=C1 STJMRWALKKWQGH-UHFFFAOYSA-N 0.000 claims 1
150000001412 amines Chemical class 0.000 abstract description 2
239000007858 starting material Substances 0.000 abstract description 2
OJUGVDODNPJEEC-UHFFFAOYSA-N phenylglyoxal Chemical compound O=CC(=O)C1=CC=CC=C1 OJUGVDODNPJEEC-UHFFFAOYSA-N 0.000 abstract 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
230000000694 effects Effects 0.000 abstract 1
230000001766 physiological effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
229910001868 water Inorganic materials 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
BCISXCSLXUAFMM-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-2-oxoacetaldehyde Chemical compound NC1=C(Cl)C=C(C(=O)C=O)C=C1Cl BCISXCSLXUAFMM-UHFFFAOYSA-N 0.000 description 1
-1 3,5-dichloro-phenylglyoxal hydrate Chemical compound 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 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 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229940106265 charcoal Drugs 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000012280 lithium aluminium hydride 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
239000011976 maleic acid Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline

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)
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)

CA212,850A 1973-11-02 1974-11-01 Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines Expired CA1041545A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2354959A DE2354959C3 (de)	1973-11-02	1973-11-02	Neues Verfahren zur Herstellung von 4-Amino-3,5 dihalogen phenyl-athanolaminen

Publications (1)

Publication Number	Publication Date
CA1041545A true CA1041545A (en)	1978-10-31

Family

ID=5897109

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA212,850A Expired CA1041545A (en)	1973-11-02	1974-11-01	Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines

Country Status (19)

Country	Link
JP (1)	JPS5855133B2 (cs)
AT (1)	AT340394B (cs)
BG (1)	BG23746A3 (cs)
CA (1)	CA1041545A (cs)
CH (1)	CH609040A5 (cs)
CS (1)	CS175487B2 (cs)
DD (1)	DD116599A5 (cs)
DE (1)	DE2354959C3 (cs)
DK (1)	DK134484C (cs)
ES (1)	ES430587A1 (cs)
FI (2)	FI60858C (cs)
HU (1)	HU168133B (cs)
NL (1)	NL7414223A (cs)
NO (1)	NO139479C (cs)
PL (1)	PL96537B1 (cs)
RO (1)	RO68703A (cs)
SE (2)	SE411546B (cs)
SU (1)	SU549079A3 (cs)
YU (1)	YU36918B (cs)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2017021982A1 (en) *	2015-08-06	2017-02-09	Vamsi Labs Ltd.	A PROCESS FOR PREPARING β AGONIST
CN111393311A (zh) *	2020-03-30	2020-07-10	苏州弘森药业股份有限公司	一种盐酸克伦特罗的环保无毒合成方法

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3714484A1 (de) *	1987-04-30	1988-11-10	Bayer Ag	Neue aminophenylethylamin-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als leistungsfoerderer
US5541188A (en) *	1987-09-15	1996-07-30	The Rowett Research Institute	Therapeutic applications of beta-adrenergic agonists
US5530029A (en) *	1987-09-15	1996-06-25	The Rowett Research Institute	Therapeutic applications of clenbuterol
GB9913083D0 (en) *	1999-06-04	1999-08-04	Novartis Ag	Organic compounds

1973
- 1973-11-02 DE DE2354959A patent/DE2354959C3/de not_active Expired
1974
- 1974-09-19 FI FI2736/74A patent/FI60858C/fi active
- 1974-09-20 AT AT756374A patent/AT340394B/de not_active IP Right Cessation
- 1974-10-02 ES ES430587A patent/ES430587A1/es not_active Expired
- 1974-10-18 CS CS7165A patent/CS175487B2/cs unknown
- 1974-10-22 DK DK552274A patent/DK134484C/da active
- 1974-10-24 YU YU2850/74A patent/YU36918B/xx unknown
- 1974-10-25 SU SU2069690A patent/SU549079A3/ru active
- 1974-10-29 BG BG028068A patent/BG23746A3/xx unknown
- 1974-10-30 CH CH1454274A patent/CH609040A5/xx not_active IP Right Cessation
- 1974-10-30 DD DD182043A patent/DD116599A5/xx unknown
- 1974-10-31 RO RO7480380A patent/RO68703A/ro unknown
- 1974-10-31 NL NL7414223A patent/NL7414223A/xx not_active Application Discontinuation
- 1974-10-31 PL PL1974175272A patent/PL96537B1/pl unknown
- 1974-11-01 JP JP49126469A patent/JPS5855133B2/ja not_active Expired
- 1974-11-01 SE SE7413786A patent/SE411546B/sv not_active IP Right Cessation
- 1974-11-01 NO NO743946A patent/NO139479C/no unknown
- 1974-11-01 HU HUTO987A patent/HU168133B/hu unknown
- 1974-11-01 CA CA212,850A patent/CA1041545A/en not_active Expired
1977
- 1977-07-28 SE SE7708686A patent/SE430057B/xx not_active IP Right Cessation
1980
- 1980-03-20 FI FI800860A patent/FI800860A7/fi not_active Application Discontinuation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2017021982A1 (en) *	2015-08-06	2017-02-09	Vamsi Labs Ltd.	A PROCESS FOR PREPARING β AGONIST
EP3331848A4 (en) *	2015-08-06	2019-07-17	Vamsi Labs Ltd.	PROCESS FOR THE PREPARATION OF BETA AGONISTS
US10414717B2 (en)	2015-08-06	2019-09-17	Vamsi Lab Ltd.	Process for preparing beta agonist
CN111393311A (zh) *	2020-03-30	2020-07-10	苏州弘森药业股份有限公司	一种盐酸克伦特罗的环保无毒合成方法

Also Published As

Publication number	Publication date
ATA756374A (de)	1977-04-15
NO139479C (no)	1979-03-21
ES430587A1 (es)	1976-09-01
JPS5071637A (cs)	1975-06-13
DK134484C (da)	1977-04-25
SE7708686L (sv)	1977-07-28
DD116599A5 (cs)	1975-12-05
FI800860A7 (fi)	1981-01-01
NO139479B (no)	1978-12-11
YU285074A (en)	1982-06-18
AT340394B (de)	1977-12-12
FI60858C (fi)	1982-04-13
FI60858B (fi)	1981-12-31
FI273674A7 (cs)	1975-05-03
NL7414223A (nl)	1975-05-07
SE430057B (sv)	1983-10-17
NO743946L (cs)	1975-05-26
CS175487B2 (cs)	1977-05-31
DE2354959A1 (de)	1975-05-15
PL96537B1 (pl)	1977-12-31
JPS5855133B2 (ja)	1983-12-08
RO68703A (ro)	1981-09-24
DE2354959B2 (de)	1979-06-07
CH609040A5 (en)	1979-02-15
DE2354959C3 (de)	1980-02-07
YU36918B (en)	1984-08-31
DK552274A (cs)	1975-06-23
SE7413786L (cs)	1975-05-05
SU549079A3 (ru)	1977-02-28
BG23746A3 (bg)	1977-10-12
SE411546B (sv)	1980-01-14
HU168133B (en)	1976-02-28
DK134484B (da)	1976-11-15

Publication	Publication Date	Title
HU193161B (en)	1987-08-28	Process for preparing new n-alkyl-norscopines
CA1041545A (en)	1978-10-31	Process for the preparation of 4-amino-3,5-dihalogen-phenyl-ethanolamines
CN111910208B (zh)	2021-07-20	一种3-苯硫基喹啉酮的电化学合成方法
RU2074854C1 (ru)	1997-03-10	Способ получения производных амидоксима о-(2-гидрокси-3-пиперидино-1-пропил)-никотиновой кислоты и их солей (варианты), чистое кристаллическое основание амидоксима о-(2-гидрокси-3-пиперидино-1-пропил)-никотиновой кислоты
KR870001899B1 (ko)	1987-10-21	1,3-디메틸-2-이미다졸리디논의 제조방법
JPS59206376A (ja)	1984-11-22	オキシラン類の製造法
EP0052333A1 (en)	1982-05-26	4-Fluoro-5-oxypyrazole derivate and preparation thereof
EP3619186B1 (en)	2021-02-17	Process for the production of semifluorinated alkanes
EP0448899B1 (en)	1994-08-31	Preparation of a para-aminodiphenylamine
JPH0597826A (ja)	1993-04-20	６−アミノ−７−フルオロ−２ｈ−１，４−ベンズオキサジン−３（４ｈ）−オンの製造法
US20230098262A1 (en)	2023-03-30	Method for synthesizing beta-cyano ketone compound
US6630593B1 (en)	2003-10-07	Process for preparing a 1-substituted 5-hydroxymethyl imidazole
US4658047A (en)	1987-04-14	Method of preparing 1,2-diaminocyclohexane tetrachloro platinum (IV) isomers
EP2837632B1 (en)	2016-05-18	Derivatives of triazabicyclo[3.2.1]octane useful for the treatment of proliferative diseases
EP3656756B1 (en)	2025-12-03	Process for the direct alpha-methylenation of ketones
CN113583039A (zh)	2021-11-02	铌或钽配合物的制备及其在催化芳香胺生成氧化偶氮苯类化合物的应用
US2688023A (en)	1954-08-31	5-(3-cyanopropyl) hydantoin and its preparation and use to prepare 5-(4-aminobutyl) hydantoin
US3733338A (en)	1973-05-15	1-oxo-isochromenes
JP4378488B2 (ja)	2009-12-09	２−アミノメチルピリミジン及びその塩の製造法
KR790001737B1 (ko)	1979-12-16	4-아미노-3,5-디할로겐-페닐-에탄올아민류의 신규 제조방법
US7358397B2 (en)	2008-04-15	Preparation of halogenated 4-aminophenols
JP3041444B2 (ja)	2000-05-15	カルバジン酸誘導体の製造法
CA1056400A (en)	1979-06-12	Process for the preparation of 1,4-naphthodinitrile
JP2001139526A (ja)	2001-05-22	ニトロソベンゼンの製法
CN120398757A (zh)	2025-08-01	一种2-丙基吡啶-4(1h)-酮醋酸盐的制备方法