BE651399A - - Google Patents

Info

Publication number: BE651399A
Authority: BE; Belgium
Prior art keywords: formula; compounds; compound; desc; solution
Prior art date: 1963-08-05

Application number

BE651399A

Other languages

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.)

1963-08-05

Filing date

1964-08-04

Publication date

1965-02-04

1963-08-05 Priority claimed from CH965063A external-priority patent/CH433302A/de

1964-08-04 Application filed filed Critical

1965-02-04 Publication of BE651399A publication Critical patent/BE651399A/fr

Links

238000002360 preparation method Methods 0.000 claims description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 34
150000001875 compounds Chemical class 0.000 claims 27
239000000243 solution Substances 0.000 claims 18
238000000034 method Methods 0.000 claims 11
150000003839 salts Chemical class 0.000 claims 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
239000003795 chemical substances by application Substances 0.000 claims 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 6
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 6
239000003960 organic solvent Substances 0.000 claims 6
125000000217 alkyl group Chemical group 0.000 claims 5
239000002585 base Substances 0.000 claims 5
229910052500 inorganic mineral Inorganic materials 0.000 claims 5
239000011707 mineral Substances 0.000 claims 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
239000002253 acid Substances 0.000 claims 4
238000001704 evaporation Methods 0.000 claims 4
230000008020 evaporation Effects 0.000 claims 4
150000007522 mineralic acids Chemical class 0.000 claims 4
150000007524 organic acids Chemical class 0.000 claims 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 4
239000000047 product Substances 0.000 claims 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 4
GBPBXBUHZSOKTH-UHFFFAOYSA-N 4-chloropiperidine Chemical compound ClC1CCNCC1 GBPBXBUHZSOKTH-UHFFFAOYSA-N 0.000 claims 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
150000007513 acids Chemical class 0.000 claims 3
125000003710 aryl alkyl group Chemical group 0.000 claims 3
238000006243 chemical reaction Methods 0.000 claims 3
239000000460 chlorine Substances 0.000 claims 3
229910052801 chlorine Inorganic materials 0.000 claims 3
-1 dissolving aids Substances 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
230000008018 melting Effects 0.000 claims 3
238000002844 melting Methods 0.000 claims 3
229950000688 phenothiazine Drugs 0.000 claims 3
238000010992 reflux Methods 0.000 claims 3
238000003756 stirring Methods 0.000 claims 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical class [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 2
125000003118 aryl group Chemical group 0.000 claims 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
229910052794 bromium Inorganic materials 0.000 claims 2
239000012320 chlorinating reagent Substances 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
229940079593 drug Drugs 0.000 claims 2
239000001530 fumaric acid Substances 0.000 claims 2
239000007789 gas Substances 0.000 claims 2
238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 2
229910052753 mercury Inorganic materials 0.000 claims 2
239000003921 oil Substances 0.000 claims 2
235000019198 oils Nutrition 0.000 claims 2
235000005985 organic acids Nutrition 0.000 claims 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 2
CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 claims 2
229950007538 pecazine Drugs 0.000 claims 2
KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 claims 2
229910000027 potassium carbonate Inorganic materials 0.000 claims 2
238000001953 recrystallisation Methods 0.000 claims 2
239000007858 starting material Substances 0.000 claims 2
239000000126 substance Substances 0.000 claims 2
235000002906 tartaric acid Nutrition 0.000 claims 2
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 2
238000009834 vaporization Methods 0.000 claims 2
230000008016 vaporization Effects 0.000 claims 2
238000005406 washing Methods 0.000 claims 2
239000008096 xylene Substances 0.000 claims 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims 1
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
101100113998 Mus musculus Cnbd2 gene Proteins 0.000 claims 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
229920002472 Starch Polymers 0.000 claims 1
235000021355 Stearic acid Nutrition 0.000 claims 1
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
150000008041 alkali metal carbonates Chemical class 0.000 claims 1
230000008485 antagonism Effects 0.000 claims 1
230000003466 anti-cipated effect Effects 0.000 claims 1
150000007514 bases Chemical class 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
238000009835 boiling Methods 0.000 claims 1
150000001805 chlorine compounds Chemical class 0.000 claims 1
238000004587 chromatography analysis Methods 0.000 claims 1
239000003086 colorant Substances 0.000 claims 1
239000012141 concentrate Substances 0.000 claims 1
230000001143 conditioned effect Effects 0.000 claims 1
238000002425 crystallisation Methods 0.000 claims 1
230000008025 crystallization Effects 0.000 claims 1
230000000911 decarboxylating effect Effects 0.000 claims 1
230000003001 depressive effect Effects 0.000 claims 1
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims 1
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims 1
239000008298 dragée Substances 0.000 claims 1
239000000975 dye Substances 0.000 claims 1
150000002148 esters Chemical class 0.000 claims 1
235000019441 ethanol Nutrition 0.000 claims 1
239000000706 filtrate Substances 0.000 claims 1
238000001914 filtration Methods 0.000 claims 1
235000003599 food sweetener Nutrition 0.000 claims 1
230000004927 fusion Effects 0.000 claims 1
235000011187 glycerol Nutrition 0.000 claims 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
239000010931 gold Substances 0.000 claims 1
229910052737 gold Inorganic materials 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
238000002347 injection Methods 0.000 claims 1
239000007924 injection Substances 0.000 claims 1
239000008101 lactose Substances 0.000 claims 1
TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
230000003278 mimic effect Effects 0.000 claims 1
239000000203 mixture Substances 0.000 claims 1
230000000701 neuroleptic effect Effects 0.000 claims 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
229910052700 potassium Inorganic materials 0.000 claims 1
239000011591 potassium Substances 0.000 claims 1
239000000843 powder Substances 0.000 claims 1
239000003755 preservative agent Substances 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
208000020016 psychiatric disease Diseases 0.000 claims 1
230000011514 reflex Effects 0.000 claims 1
230000001624 sedative effect Effects 0.000 claims 1
210000000952 spleen Anatomy 0.000 claims 1
239000003381 stabilizer Substances 0.000 claims 1
239000008107 starch Substances 0.000 claims 1
235000019698 starch Nutrition 0.000 claims 1
239000008117 stearic acid Substances 0.000 claims 1
239000000829 suppository Substances 0.000 claims 1
239000003765 sweetening agent Substances 0.000 claims 1
239000000454 talc Substances 0.000 claims 1
229910052623 talc Inorganic materials 0.000 claims 1
235000012222 talc Nutrition 0.000 claims 1
239000011975 tartaric acid Substances 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
235000015112 vegetable and seed oil Nutrition 0.000 claims 1
239000008158 vegetable oil Substances 0.000 claims 1
239000001993 wax Substances 0.000 claims 1
238000009736 wetting Methods 0.000 claims 1
238000012937 correction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 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

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)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

BE651399A 1963-08-05 1964-08-04 BE651399A (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH965063A CH433302A (de)	1963-08-05	1963-08-05	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
CH1276263		1963-10-17
CH106564		1964-01-30

Publications (1)

Publication Number	Publication Date
BE651399A true BE651399A (de)	1965-02-04

Family

ID=27172662

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE651399A BE651399A (de)	1963-08-05	1964-08-04

Country Status (3)

Country	Link
BE (1)	BE651399A (de)
FR (1)	FR3799M (de)
NL (1)	NL6408829A (de)

1964
- 1964-07-31 NL NL6408829A patent/NL6408829A/xx unknown
- 1964-08-04 BE BE651399A patent/BE651399A/fr unknown
- 1964-11-03 FR FR993650A patent/FR3799M/fr not_active Expired

Also Published As

Publication number	Publication date
FR3799M (fr)	1965-12-27
NL6408829A (de)	1965-02-08

Publication	Publication Date	Title
CA2055326A1 (fr)	1992-05-15	Derives de la n-benzoyl proline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
CA2007759A1 (fr)	1990-07-16	Derives de benzonaphtyridine-1,8, leur preparation et les compositions qui les contiennent
JPS6036436B2 (ja)	1985-08-20	１０‐〔ω‐（ベンゾイルピペリジニル）アルキル〕フエノチアジアジンおよびその酸付加塩ならびにそれらの製造法
BE651399A (de)	1965-02-04
FR2528044A1 (fr)	1983-12-09	Derives d'isoquinoleine, leur procede de preparation et medicaments les contenant
CA2166470C (en)	2001-12-18	Pharmacologically active enantiomers
Southwick et al.	1968	1-Carbamoyl-and 1-aminomethyl-1, 4-dihydropyrrolo [3, 4-b] indole derivatives. Indole formation by fragmentation of strain-barrier stabilized 2-aminoindoline derivatives
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