SE430501B - 5-substituerade n-((1-cykloalkyl-alkyl-pyrrolidin-2-yl)-metyl)-2-metoxi-bens-amider med terapeutiska egenskaper och deras framstellning - Google Patents

5-substituerade n-((1-cykloalkyl-alkyl-pyrrolidin-2-yl)-metyl)-2-metoxi-bens-amider med terapeutiska egenskaper och deras framstellning

Info

Publication number: SE430501B
Authority: SE; Sweden
Prior art keywords: methoxy; mol; alkyl; pyrrolidin; methyl
Prior art date: 1978-02-27

Application number

SE7901708A

Other languages

English (en)

Swedish (sv)

Other versions

SE7901708L (sv

Inventor

J P Kaplan

H Najer

D C L Obitz

Original Assignee

Synthelabo

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.)

1978-02-27

Filing date

1979-02-26

Publication date

1983-11-21

1979-02-26 Application filed by Synthelabo filed Critical Synthelabo

1979-08-28 Publication of SE7901708L publication Critical patent/SE7901708L/xx

1983-11-21 Publication of SE430501B publication Critical patent/SE430501B/sv

Links

229940054066 benzamide antipsychotics Drugs 0.000 title 1
230000001225 therapeutic effect Effects 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 8
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000005711 Benzoic acid Substances 0.000 claims description 3
238000000034 method Methods 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 2
125000004414 alkyl thio group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
239000003921 oil Substances 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
229910000027 potassium carbonate Inorganic materials 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
QFIYFROFRTUSPW-UHFFFAOYSA-N [1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1CC1 QFIYFROFRTUSPW-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
-1 1-cyclopropylmethyl-pyrrolidin-2-yl Chemical group 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
KZZUPJSYJCNYMW-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioyl chloride Chemical compound COC1=CC=C(C)C=C1C(Cl)=S KZZUPJSYJCNYMW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000005457 ice water Substances 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
IUTPSVNWIWQIDX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)pyrazol-4-yl]ethanone Chemical compound C1=C(C(=O)C)C=NN1C1=CC=C(Cl)C=C1 IUTPSVNWIWQIDX-UHFFFAOYSA-N 0.000 description 1
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 description 1
SXAMGRAIZSSWIH-UHFFFAOYSA-N 2-[3-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,2,4-oxadiazol-5-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NOC(=N1)CC(=O)N1CC2=C(CC1)NN=N2 SXAMGRAIZSSWIH-UHFFFAOYSA-N 0.000 description 1
XYTWILFWSVFPHB-UHFFFAOYSA-N 2-methoxy-5-(trifluoromethyl)benzamide Chemical compound COC1=CC=C(C(F)(F)F)C=C1C(N)=O XYTWILFWSVFPHB-UHFFFAOYSA-N 0.000 description 1
AJGHIKKOAMKRMC-UHFFFAOYSA-N 2-methoxy-5-methylbenzenecarbothioamide Chemical compound COC1=CC=C(C)C=C1C(N)=S AJGHIKKOAMKRMC-UHFFFAOYSA-N 0.000 description 1
OUBZCDOQEMLMAB-UHFFFAOYSA-N 5-chlorosulfonyl-2-methoxybenzoic acid Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1C(O)=O OUBZCDOQEMLMAB-UHFFFAOYSA-N 0.000 description 1
BOLLTSUCKRNILK-UHFFFAOYSA-N COC1=C(C(=S)O)C=C(C=C1)CC Chemical compound COC1=C(C(=S)O)C=C(C=C1)CC BOLLTSUCKRNILK-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 0.000 description 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
208000012545 Psychophysiologic disease Diseases 0.000 description 1
208000028017 Psychotic disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 1
229960004046 apomorphine Drugs 0.000 description 1
SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
KIWBPDUYBMNFTB-UHFFFAOYSA-M ethyl sulfate Chemical compound CCOS([O-])(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-M 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
208000024335 physical disease Diseases 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups

Landscapes

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

SE7901708A 1978-02-27 1979-02-26 5-substituerade n-((1-cykloalkyl-alkyl-pyrrolidin-2-yl)-metyl)-2-metoxi-bens-amider med terapeutiska egenskaper och deras framstellning SE430501B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7805580A FR2418226A1 (fr)	1978-02-27	1978-02-27	Methoxy-2 alkylthio-5 benzamides et leur application en therapeutique

Publications (2)

Publication Number	Publication Date
SE7901708L SE7901708L (sv)	1979-08-28
SE430501B true SE430501B (sv)	1983-11-21

Family

ID=9205110

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7901708A SE430501B (sv)	1978-02-27	1979-02-26	5-substituerade n-((1-cykloalkyl-alkyl-pyrrolidin-2-yl)-metyl)-2-metoxi-bens-amider med terapeutiska egenskaper och deras framstellning

Country Status (23)

Country	Link
JP (1)	JPS54122269A (fr)
AT (1)	AT373581B (fr)
AU (1)	AU521854B2 (fr)
BE (1)	BE874490A (fr)
CA (1)	CA1105937A (fr)
CH (1)	CH637378A5 (fr)
DE (1)	DE2907377A1 (fr)
DK (1)	DK82379A (fr)
ES (1)	ES478073A1 (fr)
FI (1)	FI790658A7 (fr)
FR (1)	FR2418226A1 (fr)
GB (1)	GB2014995B (fr)
GR (1)	GR66973B (fr)
IE (1)	IE47897B1 (fr)
IL (1)	IL56747A0 (fr)
IT (1)	IT1114210B (fr)
LU (1)	LU80976A1 (fr)
NL (1)	NL7901472A (fr)
NO (1)	NO790648L (fr)
NZ (1)	NZ189771A (fr)
PT (1)	PT69290A (fr)
SE (1)	SE430501B (fr)
ZA (1)	ZA799808B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1988009404A1 (fr) *	1987-05-25	1988-12-01	Foreshore Protection Pty Limited	Matelas de revetement de sol

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2245628B1 (fr) *	1973-09-28	1977-03-11	Ile De France

1978
- 1978-02-27 FR FR7805580A patent/FR2418226A1/fr active Granted
1979
- 1979-02-26 ZA ZA00799808A patent/ZA799808B/xx unknown
- 1979-02-26 IT IT20542/79A patent/IT1114210B/it active
- 1979-02-26 JP JP2247679A patent/JPS54122269A/ja active Pending
- 1979-02-26 AU AU44604/79A patent/AU521854B2/en not_active Ceased
- 1979-02-26 NL NL7901472A patent/NL7901472A/xx not_active Application Discontinuation
- 1979-02-26 NZ NZ189771A patent/NZ189771A/xx unknown
- 1979-02-26 SE SE7901708A patent/SE430501B/sv unknown
- 1979-02-26 CA CA322,283A patent/CA1105937A/fr not_active Expired
- 1979-02-26 DK DK82379A patent/DK82379A/da not_active Application Discontinuation
- 1979-02-26 CH CH188379A patent/CH637378A5/fr not_active IP Right Cessation
- 1979-02-26 DE DE19792907377 patent/DE2907377A1/de not_active Withdrawn
- 1979-02-26 PT PT69290A patent/PT69290A/fr unknown
- 1979-02-26 ES ES478073A patent/ES478073A1/es not_active Expired
- 1979-02-26 NO NO790648A patent/NO790648L/no unknown
- 1979-02-27 FI FI790658A patent/FI790658A7/fi not_active Application Discontinuation
- 1979-02-27 IL IL56747A patent/IL56747A0/xx unknown
- 1979-02-27 GB GB7906954A patent/GB2014995B/en not_active Expired
- 1979-02-27 AT AT0149479A patent/AT373581B/de not_active IP Right Cessation
- 1979-02-27 BE BE0/193730A patent/BE874490A/fr not_active IP Right Cessation
- 1979-02-27 LU LU80976A patent/LU80976A1/fr unknown
- 1979-02-27 GR GR58492A patent/GR66973B/el unknown
- 1979-08-08 IE IE558/79A patent/IE47897B1/en unknown

Also Published As

Publication number	Publication date
IT7920542A0 (it)	1979-02-26
IE47897B1 (en)	1984-07-11
LU80976A1 (fr)	1980-09-24
DE2907377A1 (de)	1979-09-06
ATA149479A (de)	1983-06-15
AU521854B2 (en)	1982-05-06
FR2418226A1 (fr)	1979-09-21
GB2014995B (en)	1982-07-28
PT69290A (fr)	1979-03-01
FR2418226B1 (fr)	1980-11-07
NZ189771A (en)	1980-11-14
JPS54122269A (en)	1979-09-21
IL56747A0 (en)	1979-05-31
GR66973B (fr)	1981-05-15
AT373581B (de)	1984-02-10
NO790648L (no)	1979-08-28
IT1114210B (it)	1986-01-27
ZA799808B (en)	1980-06-25
CH637378A5 (fr)	1983-07-29
CA1105937A (fr)	1981-07-28
AU4460479A (en)	1979-09-06
BE874490A (fr)	1979-08-27
GB2014995A (en)	1979-09-05
IE790558L (en)	1979-08-27
ES478073A1 (es)	1979-05-16
FI790658A7 (fi)	1979-08-28
DK82379A (da)	1979-08-28
SE7901708L (sv)	1979-08-28
NL7901472A (nl)	1979-08-29

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CA1180324A (fr)	1985-01-02	Inhibiteurs de la collagenase des mammiferes
EP0352613A2 (fr)	1990-01-31	Aminométhyl-tétralines substituées et leurs analogues hétérocycliques
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CH619463A5 (fr)	1980-09-30
EP0496238A1 (fr)	1992-07-29	Benzoxazépines et benzothiazépines substituées, procédé pour leur préparation et leur application comme medicaments
FR2468601A1 (fr)	1981-05-08	Nouveaux derives de flavanne utiles notamment comme anticonvulsivants
US6864374B2 (en)	2005-03-08	Synthesis of r(+)α-lipoic acid
WO2012098501A1 (fr)	2012-07-26	Co-cristaux de fébuxostat
DK169921B1 (da)	1995-04-03	2-Iminobenzothiazolin-forbindelser, fremgangsmåder til deres fremstilling, lægemidler med indhold deraf og deres anvendelse til fremstilling af lægemidler.
US20180186753A1 (en)	2018-07-05	Processes for the preparation of pesticidal compounds
CH639078A5 (fr)	1983-10-31	Amides derives d'acides carboxyliques-5 pyrimidiniques, leur preparation et medicaments les contenant.
AT400717B (de)	1996-03-25	Neue guanidin- und amidinsalze von 7-amino-3- hydroxymethyl-3-cephem-4-carbonsäure
SE430501B (sv)	1983-11-21	5-substituerade n-((1-cykloalkyl-alkyl-pyrrolidin-2-yl)-metyl)-2-metoxi-bens-amider med terapeutiska egenskaper och deras framstellning
DE69703115T2 (de)	2001-08-23	Zwischenprodukte um 2-imidazolin-5onederivate herzustellen.
DE3884508T2 (de)	1994-02-03	Cystein-Derivate mit Expectorans-Wirkung.
DE69713128T2 (de)	2003-03-20	4-(1-piperazinyl)benzosäurederivate, verfahren zu ihrer herstellung und ihre therapeutischen verwendungen
SU880251A3 (ru)	1981-11-07	Способ получени производных тиохромана или их солей
DE68912887T2 (de)	1994-05-26	Thiophen-2-carboxamid-Derivate und ihre Verwendung als pharmazeutische Mittel.
PL111253B1 (en)	1980-08-30	Process for preparing novel derivatives of dibenzo/d,g//1,3,6/dioxazocin
BONVICINO et al.	1959	Studies on Some Oxidation and Reduction Products of Thiamine. II. 1 Thiamine Disulfide-Thioglycolic Acid Reaction. 2-4
US6613919B2 (en)	2003-09-02	Method for resolving racemic mixtures of 5-substituted 4-hydroxy-2-furanones
DE68912865T2 (de)	1994-05-26	Organische Verbindungen und ihre Verwendung als Pharmazeutika.