CH377833A - Verfahren zur Herstellung eines neuen Hustenmittels - Google Patents

Verfahren zur Herstellung eines neuen Hustenmittels

Info

Publication number: CH377833A
Authority: CH; Switzerland
Prior art keywords: sep; pyridazinone; methyl; carboxylic acid; dihydro
Prior art date: 1958-07-17

Application number

CH7575959A

Other languages

German (de)

English (en)

Inventor

Teotino Uberto

Maffii Giulio

Original Assignee

Lepetit Spa

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.)

1958-07-17

Filing date

1959-07-14

Publication date

1964-05-31

1958-07-17 Priority claimed from GB22991/58A external-priority patent/GB893278A/en

1959-07-14 Application filed by Lepetit Spa filed Critical Lepetit Spa

1964-05-31 Publication of CH377833A publication Critical patent/CH377833A/de

Links

239000003434 antitussive agent Substances 0.000 title description 7
229940124584 antitussives Drugs 0.000 title description 7
238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
238000000034 method Methods 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000003814 drug Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
229940079593 drug Drugs 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
206010011224 Cough Diseases 0.000 description 3
UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 3
235000019441 ethanol Nutrition 0.000 description 3
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 3
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 3
230000003533 narcotic effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000007665 chronic toxicity Effects 0.000 description 2
231100000160 chronic toxicity Toxicity 0.000 description 2
229960004126 codeine Drugs 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
WOSVNRNLAPEKDN-UHFFFAOYSA-N methyl 6-oxo-4,5-dihydro-1h-pyridazine-3-carboxylate Chemical compound COC(=O)C1=NNC(=O)CC1 WOSVNRNLAPEKDN-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000011343 solid material Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
LXFKHPXXAPOYCC-UHFFFAOYSA-N 1-methyl-6-oxo-4,5-dihydropyridazine-3-carboxamide Chemical compound CN1N=C(C(N)=O)CCC1=O LXFKHPXXAPOYCC-UHFFFAOYSA-N 0.000 description 1
KPGXRSRHYNQIFN-UHFFFAOYSA-L 2-oxoglutarate(2-) Chemical compound [O-]C(=O)CCC(=O)C([O-])=O KPGXRSRHYNQIFN-UHFFFAOYSA-L 0.000 description 1
WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
MTJLHSQWYQRXMK-UHFFFAOYSA-N C(CCC)N1N=CCCC1=O Chemical compound C(CCC)N1N=CCCC1=O MTJLHSQWYQRXMK-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 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 description 1
241000699670 Mus sp. Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
RVCABEYSXYYMSH-UHFFFAOYSA-N methyl 1-methyl-6-oxo-4,5-dihydropyridazine-3-carboxylate Chemical compound COC(=O)C1=NN(C)C(=O)CC1 RVCABEYSXYYMSH-UHFFFAOYSA-N 0.000 description 1
IHRPJNDVWBJCEH-UHFFFAOYSA-N methyl 4-(butylamino)benzoate Chemical compound CCCCNC1=CC=C(C(=O)OC)C=C1 IHRPJNDVWBJCEH-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
229920000847 nonoxynol Polymers 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/18—Sulfonamides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH7575959A 1958-07-17 1959-07-14 Verfahren zur Herstellung eines neuen Hustenmittels CH377833A (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB22991/58A GB893278A (en)	1958-07-17	1958-07-17	Pyridazone amide derivatives
GB3931158		1958-12-05

Publications (1)

Publication Number	Publication Date
CH377833A true CH377833A (de)	1964-05-31

Family

ID=26256225

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7575959A CH377833A (de)	1958-07-17	1959-07-14	Verfahren zur Herstellung eines neuen Hustenmittels

Country Status (2)

Country	Link
CH (1)	CH377833A (fr)
FR (1)	FR148M (fr)

1959
- 1959-07-14 CH CH7575959A patent/CH377833A/de unknown
1960
- 1960-08-08 FR FR835250A patent/FR148M/fr not_active Expired

Also Published As

Publication number	Publication date
FR148M (fr)	1961-02-06

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DE69530205T2 (de)	2004-02-05	Heterocyclisch kondensierte morphinoid-derivate
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DE3220831A1 (de)	1983-12-08	N-(2-methoxyethyl)-noroxymorphon, dessen saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung
DE1620541C3 (de)	1975-09-25	Neue in 3-Stellung substituierte 6,8-Dibrom-tetrahydro-chinazoline
DE1963317A1 (de)	1970-07-09	Chemische Verfahren und Produkte
DE2513136C3 (de)	1981-04-30	N-(1-Benzylpiperid-4-yl)-benzamide, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate
DE2107871C3 (fr)	1974-02-28
CH377833A (de)	1964-05-31	Verfahren zur Herstellung eines neuen Hustenmittels
DE3121175A1 (de)	1982-12-16	Erythro-1,2,3-triphenyl-1-pentanon-derivate sowie verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
EP0003286B1 (fr)	1982-03-24	Dérivés d'alcaloides ergopeptidiques, procédé pour leur préparation et compositions pharmaceutiques les contenant
DE2717062C2 (de)	1982-11-25	Arzneimittel mit antitussiver Wirkung
DE2634191A1 (de)	1977-02-17	Gem-diarylverbindungen und sie enthaltende arzneimittel
AT212322B (de)	1960-12-12	Verfahren zur Herstellung von neuen Pyridazinon-Derivaten
DE2445002C2 (de)	1984-11-22	N,N'-(Pyridin-diyl)-dioxamidsäurederivate und deren pharmazeutisch verträgliche Säureadditionssalze, Verfahren zu deren Herstellung und dieselben enthaltende pharmazeutische Mittel
DE2125892C3 (de)	1980-07-03	23-Dihydro-S-trifIuormethyl-lH- dibenzo [23 zu 6,7] thiepine [4,5] pyrrole, Verfahren zu ihrer Herstellung und diese enthaltende therapeutsche Präparate
US3256149A (en)	1966-06-14	Compositions comprising an alkaloid of mitragyna speciosa and methods of using same
DE2227846A1 (de)	1973-01-04	Phenoxyessigsaeure-derivate und verfahren zu ihrer herstellung
DE1518311B1 (de)	1972-05-31	N-(2-Diaethylaminoaethyl)-2-methoxy-3,4- bzw. 4,5-methylendioxybenzamid und deren pharmakologisch nicht giftige Saeureadditionssalze
EP0085893A2 (fr)	1983-08-17	Pyridobenzodiazépinones, procédé pour leur préparation et compositions pharmaceutiques les contenant