NO131127B - - Google Patents

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Publication number: NO131127B
Authority: NO; Norway
Prior art keywords: formula; chloro; salt; added; butylamine
Prior art date: 1969-12-04

Application number

NO04645/70A

Other languages

English (en)

Norwegian (no)

Other versions

NO131127C (da

Inventor

N Us Mehta

Original Assignee

Wellcome Found

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.)

1969-12-04

Filing date

1970-12-03

Publication date

1974-12-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=10483336&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=NO131127(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1970-12-03 Application filed by Wellcome Found filed Critical Wellcome Found

1971-09-02 Priority to NO327871A priority Critical patent/NO133663C/no

1974-12-30 Publication of NO131127B publication Critical patent/NO131127B/no

1975-04-09 Publication of NO131127C publication Critical patent/NO131127C/no

Links

150000001875 compounds Chemical class 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 9
230000001430 anti-depressive effect Effects 0.000 claims description 8
239000000935 antidepressant agent Substances 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
229910052731 fluorine Chemical group 0.000 claims description 2
239000011737 fluorine Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
150000003333 secondary alcohols Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000010410 layer Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
150000002576 ketones Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
-1 aliphatic ketones Chemical class 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical class CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 5
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000007792 addition Methods 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
PQWGFUFROKIJBO-UHFFFAOYSA-N 1-(3-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(Cl)=C1 PQWGFUFROKIJBO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
238000003756 stirring Methods 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
230000003001 depressive effect Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
239000000155 melt Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
RPMOHVRRKYJFSB-UHFFFAOYSA-N 1-(3-fluorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(F)=C1 RPMOHVRRKYJFSB-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
WPDWOCRJBPXJFM-UHFFFAOYSA-N 2-bromo-1-phenylpropan-1-one Chemical class CC(Br)C(=O)C1=CC=CC=C1 WPDWOCRJBPXJFM-UHFFFAOYSA-N 0.000 description 1
AXCPQHPNAZONTH-UHFFFAOYSA-N 2-chloro-1-phenylpropan-1-one Chemical compound CC(Cl)C(=O)C1=CC=CC=C1 AXCPQHPNAZONTH-UHFFFAOYSA-N 0.000 description 1
JHWIEAWILPSRMU-UHFFFAOYSA-N 2-methyl-3-pyrimidin-4-ylpropanoic acid Chemical compound OC(=O)C(C)CC1=CC=NC=N1 JHWIEAWILPSRMU-UHFFFAOYSA-N 0.000 description 1
WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
JZTPKAROPNTQQV-UHFFFAOYSA-N 3-fluorobenzonitrile Chemical compound FC1=CC=CC(C#N)=C1 JZTPKAROPNTQQV-UHFFFAOYSA-N 0.000 description 1
HEYVINCGKDONRU-UHFFFAOYSA-N Bupropion hydrochloride Chemical compound Cl.CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 HEYVINCGKDONRU-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
102000010909 Monoamine Oxidase Human genes 0.000 description 1
108010062431 Monoamine oxidase Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
238000006036 Oppenauer oxidation reaction Methods 0.000 description 1
241000700159 Rattus Species 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000003517 fume Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002315 pressor effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/14—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated
- C07C225/16—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
- 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
- A61P25/24—Antidepressants
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Psychiatry (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (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)

NO4645/70A 1969-12-04 1970-12-03 NO131127C (da)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO327871A NO133663C (da)	1969-12-04	1971-09-02

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB5923169		1969-12-04

Publications (2)

Publication Number	Publication Date
NO131127B true NO131127B (da)	1974-12-30
NO131127C NO131127C (da)	1975-04-09

Family

ID=10483336

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO4645/70A NO131127C (da)	1969-12-04	1970-12-03

Country Status (29)

Country	Link
US (1)	US3819706A (da)
JP (1)	JPS4825179B1 (da)
AR (2)	AR192302A1 (da)
AT (2)	AT307389B (da)
BE (1)	BE759838A (da)
CA (1)	CA977777A (da)
CH (2)	CH569693A5 (da)
CS (1)	CS172338B2 (da)
DE (2)	DE2059618C3 (da)
DK (1)	DK134984B (da)
EG (1)	EG10507A (da)
ES (1)	ES386127A1 (da)
FI (1)	FI53813C (da)
FR (1)	FR2081326B1 (da)
HK (1)	HK78476A (da)
IE (1)	IE34788B1 (da)
IL (1)	IL35781A (da)
IT (1)	IT8047948A0 (da)
MT (1)	MTP680B (da)
MY (1)	MY7700107A (da)
NL (1)	NL172148C (da)
NO (1)	NO131127C (da)
PH (1)	PH9351A (da)
PL (1)	PL74637B1 (da)
RO (1)	RO57979A (da)
SE (1)	SE377933B (da)
YU (1)	YU34269B (da)
ZA (1)	ZA708179B (da)
ZM (1)	ZM14070A1 (da)

Families Citing this family (197)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4021492A (en) *	1975-03-24	1977-05-03	Sandoz, Inc.	Dibromination process
SE414305B (sv) *	1976-08-25	1980-07-21	Astra Laekemedel Ab	Analogiforfarande for framstellning av eventuellt substituerade 2-amino-6-fenyl-5,5dimetyl 3-hexanon med antidepressiv aktivitet
US4318791A (en) *	1977-12-22	1982-03-09	Ciba-Geigy Corporation	Use of aromatic-aliphatic ketones as photo sensitizers
FR2430933A1 (fr) *	1978-07-13	1980-02-08	Synthelabo	Derives de propiophenone et leur application en therapeutique
US4347257A (en) *	1979-10-09	1982-08-31	Burroughs Wellcome Co.	Prolactin suppression in mammals
FR2486074A1 (fr) *	1979-12-14	1982-01-08	Lafon Labor	Derives de fluorophenacyl-amine, leur procede de preparation et leur application en therapeutique
EP0038071B1 (en) *	1980-04-14	1984-11-14	The Wellcome Foundation Limited	New unlabelled and radioactive labelled derivatives of butylamino propiophenone, their preparation, immunogens obtained from the unlabelled derivatives and a process for immunogen preparation, antisera raised using the immunogens and a method for raising antisera, a radioimmunoassay method and a test kit for use in the assay method
DE3165495D1 (en) *	1981-03-23	1984-09-20	Lafon Labor	Derivatives of fluorophenacyl amines and their therapeutic use
JPS57169450A (en) *	1981-04-13	1982-10-19	Lafon Labor	Fluorophenacyl-amine derivative and application to remedy
US4393078A (en) *	1982-03-15	1983-07-12	Burroughs Wellcome Co.	Bupropion and ethanol
USRE33994E (en) *	1983-08-16	1992-07-14	Burroughs Wellcome Co.	Pharmaceutical delivery system
US4507323A (en) *	1984-07-25	1985-03-26	Burroughs Wellcome Co.	Treatment of psychosexual dysfunctions
FR2569184A1 (fr) *	1984-08-20	1986-02-21	Lafon Labor	Derives de 1-(aminophenyl) therapeutique et leur procede de preparation
FR2569185B1 (fr) *	1984-08-20	1986-09-05	Lafon Labor	Derives de 1-(aminophenyl)-2-amino-ethanone, procede de preparation et utilisation en therapeutique
US5236922A (en) *	1984-08-20	1993-08-17	Laboratoire L. Lafon	Method for treating depression using 1-(aminophenyl)-2-aminopropanone derivatives
GB9217295D0 (en) *	1992-08-14	1992-09-30	Wellcome Found	Controlled released tablets
US5358970A (en) *	1993-08-12	1994-10-25	Burroughs Wellcome Co.	Pharmaceutical composition containing bupropion hydrochloride and a stabilizer
GB9315856D0 (en) *	1993-07-30	1993-09-15	Wellcome Found	Stabilized pharmaceutical
US5541231A (en) *	1993-07-30	1996-07-30	Glaxo Wellcome Inc.	Stabilized Pharmaceutical
US5753712A (en) *	1994-02-18	1998-05-19	Pinsker; Walter	Treatment of migraine headaches and formulations
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CN106699527A (zh) *	2016-12-07	2017-05-24	三峡大学	一种间氯苯丙酮的合成方法
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US11730706B1 (en)	2022-07-07	2023-08-22	Antecip Bioventures Ii Llc	Treatment of depression in certain patient populations

0
- BE BE759838D patent/BE759838A/xx not_active IP Right Cessation
1970
- 1970-11-28 MT MT680A patent/MTP680B/xx unknown
- 1970-11-30 US US00093852A patent/US3819706A/en not_active Expired - Lifetime
- 1970-12-03 ZM ZM140/70A patent/ZM14070A1/xx unknown
- 1970-12-03 JP JP45106403A patent/JPS4825179B1/ja active Pending
- 1970-12-03 DE DE2059618A patent/DE2059618C3/de not_active Expired
- 1970-12-03 DE DE19702064934 patent/DE2064934A1/de active Pending
- 1970-12-03 FI FI3257/70A patent/FI53813C/fi active
- 1970-12-03 PL PL1970144790A patent/PL74637B1/pl unknown
- 1970-12-03 ES ES386127A patent/ES386127A1/es not_active Expired
- 1970-12-03 FR FR7043470A patent/FR2081326B1/fr not_active Expired
- 1970-12-03 IL IL35781A patent/IL35781A/en unknown
- 1970-12-03 ZA ZA708179A patent/ZA708179B/xx unknown
- 1970-12-03 NO NO4645/70A patent/NO131127C/no unknown
- 1970-12-03 EG EG503/70A patent/EG10507A/xx active
- 1970-12-03 IE IE1551/70A patent/IE34788B1/xx unknown
- 1970-12-03 YU YU2945/70A patent/YU34269B/xx unknown
- 1970-12-03 CA CA099,790A patent/CA977777A/en not_active Expired
- 1970-12-03 NL NLAANVRAGE7017687,A patent/NL172148C/xx not_active IP Right Cessation
- 1970-12-03 AT AT977571A patent/AT307389B/de not_active IP Right Cessation
- 1970-12-03 DK DK617070AA patent/DK134984B/da unknown
- 1970-12-03 AT AT1087470A patent/AT302276B/de active
- 1970-12-03 SE SE7016354A patent/SE377933B/xx unknown
- 1970-12-04 RO RO65195A patent/RO57979A/ro unknown
- 1970-12-04 CH CH1802170A patent/CH569693A5/xx not_active IP Right Cessation
- 1970-12-04 CS CS8205A patent/CS172338B2/cs unknown
- 1970-12-04 CH CH819373A patent/CH574907A5/xx not_active IP Right Cessation
- 1970-12-04 AR AR232792A patent/AR192302A1/es active
- 1970-12-22 PH PH12063*UA patent/PH9351A/en unknown
1971
- 1971-12-01 AR AR239359A patent/AR198945A1/es active
1976
- 1976-12-09 HK HK784/76*UA patent/HK78476A/xx unknown
1977
- 1977-12-31 MY MY1977107A patent/MY7700107A/xx unknown
1980
- 1980-02-19 IT IT8047948A patent/IT8047948A0/it unknown

Also Published As

Publication number	Publication date
ZA708179B (en)	1972-07-26
IE34788B1 (en)	1975-08-20
IL35781A0 (en)	1971-02-25
MTP680B (en)	1971-09-11
RO57979A (da)	1975-03-15
DE2059618C3 (de)	1981-04-16
YU294570A (en)	1978-10-31
BE759838A (fr)	1971-06-03
IE34788L (en)	1971-06-04
PL74637B1 (da)	1974-12-31
NL172148B (nl)	1983-02-16
DE2059618A1 (de)	1971-10-07
NL7017687A (da)	1971-06-08
AR198945A1 (es)	1974-07-31
CA977777A (en)	1975-11-11
DE2059618B2 (de)	1980-07-10
AT302276B (de)	1972-10-10
YU34269B (en)	1979-04-30
EG10507A (en)	1976-03-31
CH569693A5 (da)	1975-11-28
CH574907A5 (da)	1976-04-30
NO131127C (da)	1975-04-09
IL35781A (en)	1973-06-29
ZM14070A1 (en)	1972-08-21
NL172148C (nl)	1983-07-18
DK134984B (da)	1977-02-21
PH9351A (en)	1975-10-06
DK134984C (da)	1977-07-11
FI53813C (fi)	1978-08-10
ES386127A1 (es)	1973-12-16
FI53813B (fi)	1978-05-02
US3819706A (en)	1974-06-25
IT8047948A0 (it)	1980-02-19
CS172338B2 (da)	1976-12-29
FR2081326B1 (da)	1974-08-30
MY7700107A (en)	1977-12-31
DE2064934A1 (de)	1971-10-21
SE377933B (da)	1975-08-04
FR2081326A1 (da)	1971-12-03
AT307389B (de)	1973-05-25
HK78476A (en)	1976-12-17
JPS4825179B1 (da)	1973-07-26
AR192302A1 (es)	1973-02-14

Publication	Publication Date	Title
NO131127B (da)	1974-12-30
Gilman et al.	1956	Some reactions of o-halobromobenzenes with n-butyllithium
US3885046A (en)	1975-05-20	Meta chloro or fluoro substituted alpha-T-butylaminopropionphenones in the treatment of depression
Kuehne et al.	1968	Reactions of ynamines
Birkinshaw et al.	1936	Studies in the biochemistry of micro-organisms: penicillic acid, a metabolic product of Penicillium puberulum Bainier and P. cylopium Westling
US3050559A (en)	1962-08-21	Substituted phenylcyclopropylamjnes
SK286290A3 (en)	1997-04-09	Manufacturing process of pyrazoles
IE50998B1 (en)	1986-09-03	Substituted oxiranecarboxylic acids,processes for their preparation,their use and medicaments containing them
US3345416A (en)	1967-10-03	Preparation and rearrangement of beta-ketosulfoxides
US2451740A (en)	1948-10-19	Process for the manufacture of an aldehyde
US3647879A (en)	1972-03-07	Alpha-haloacetylanilino-alpha-alkoxyacetophenones
US3105090A (en)	1963-09-24	Derivatives of alkyl benzoic acid and salts thereof with bases
JPH02292263A (ja)	1990-12-03	１―メチル―３―アルキル―５―ピラゾールカルボン酸エステル類の製造法
US2218349A (en)	1940-10-15	Halogenated derivatives of aceto propyl alcohol
US4052409A (en)	1977-10-04	Disubstituted triphenylmethylimidazoles
DK145741B (da)	1983-02-14	Fremgangsmaade til fremstilling af 6-chlor-alfa-methyl-carbazol-2-eddikesyre
EP0017264B1 (en)	1983-02-02	Bicyclic lactams and a process for their preparation
US2545433A (en)	1951-03-20	3-nitro-4-hydroxy-thiophanes
JPS59137478A (ja)	1984-08-07	メチル−２−テトラデシルグリシデ−トの製法
US3178437A (en)	1965-04-13	Process for simultaneously producing prolinols and 3-hydroxy-piperidines
DK158309B (da)	1990-04-30	Fremgangsmaade til stereospecifik fremstilling af (z)-1-(4-klorfenyl)-2-(1h-imidazol-1-yl)-0-(4-klorbenzyl)-aetanonoxim eller (z)-1-(2,4-diklorfenyl)-2-(1h-imidazol-1-yl)-0-(2,4-diklorbenzyl)-aetanonoxim eller nitrat-additionssalte deraf
JPS5919545B2 (ja)	1984-05-07	新規三環式かご状アミン化合物
US2302671A (en)	1942-11-24	Halogenated derivatives of aceto propane
Fuson et al.	1938	The Action of Methylmagnesium Halides on 2, 4, 6-Trisubstituted Benzoyl Chlorides
NO137900B (no)	1978-02-06	Analogifremgangsm}te til fremstilling av terapeutisk aktive, basisk substituerte teofyllin-derivater