NO134115B - - Google Patents

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Info

Publication number: NO134115B
Authority: NO; Norway
Prior art keywords: furan; formula; hydrochloride; ethyl; acid addition
Prior art date: 1971-01-27

Application number

NO192/72A

Other languages

English (en)

Norwegian (no)

Other versions

NO134115C (nl

Inventor

F Binon

A Areschka

Original Assignee

Labaz

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.)

1971-01-27

Filing date

1972-01-26

Publication date

1976-05-10

1972-01-26 Application filed by Labaz filed Critical Labaz

1976-05-10 Publication of NO134115B publication Critical patent/NO134115B/no

1976-08-18 Publication of NO134115C publication Critical patent/NO134115C/no

Links

150000001875 compounds Chemical class 0.000 claims description 29
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 14
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000002585 base Substances 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
150000002462 imidazolines Chemical class 0.000 claims description 3
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
239000000243 solution Substances 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
-1 ethanol Chemical compound 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000005526 vasoconstrictor agent Substances 0.000 description 9
230000000694 effects Effects 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000009792 diffusion process Methods 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
UFQDKRWQSFLPQY-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound Cl.C1CN=CN1 UFQDKRWQSFLPQY-UHFFFAOYSA-N 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
150000002240 furans Chemical class 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
DJDFFEBSKJCGHC-UHFFFAOYSA-N Naphazoline Chemical compound Cl.C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 DJDFFEBSKJCGHC-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000007789 gas Substances 0.000 description 4
210000004877 mucosa Anatomy 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
RWCHGCSLPRNFRX-UHFFFAOYSA-N 2-(2-ethyl-1-benzofuran-3-yl)acetonitrile Chemical compound C1=CC=C2C(CC#N)=C(CC)OC2=C1 RWCHGCSLPRNFRX-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
210000004081 cilia Anatomy 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000007654 immersion Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229960004760 naphazoline hydrochloride Drugs 0.000 description 3
210000002850 nasal mucosa Anatomy 0.000 description 3
239000002904 solvent Substances 0.000 description 3
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 2
WAJGQJWHIKUPRN-UHFFFAOYSA-N 3-(chloromethyl)-2-ethyl-1-benzofuran Chemical compound C(C)C1=C(C2=C(O1)C=CC=C2)CCl WAJGQJWHIKUPRN-UHFFFAOYSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
210000004204 blood vessel Anatomy 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
230000001886 ciliary effect Effects 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
OIJWIKJZWZRMBZ-UHFFFAOYSA-N ethyl 2-(2-ethyl-1-benzofuran-3-yl)-2-iminoacetate hydrochloride Chemical compound Cl.C(C)C=1OC2=C(C1C(C(=O)OCC)=N)C=CC=C2 OIJWIKJZWZRMBZ-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000004899 motility Effects 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
210000003437 trachea Anatomy 0.000 description 2
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
BITVLJAJVLSVLZ-UHFFFAOYSA-N 2-(2-butyl-1-benzofuran-3-yl)acetonitrile Chemical compound C(CCC)C1=C(C2=C(O1)C=CC=C2)CC#N BITVLJAJVLSVLZ-UHFFFAOYSA-N 0.000 description 1
YDDYHDKRIBOHOT-UHFFFAOYSA-N 2-[(2-ethyl-1-benzofuran-3-yl)methyl]-4,5-dihydro-1h-imidazol-3-ium;chloride Chemical compound [Cl-].CCC=1OC2=CC=CC=C2C=1CC1=[NH+]CCN1 YDDYHDKRIBOHOT-UHFFFAOYSA-N 0.000 description 1
AQFDXZOGFHBNRW-UHFFFAOYSA-N 2-butyl-3-(chloromethyl)-1-benzofuran Chemical compound C(CCC)C1=C(C2=C(O1)C=CC=C2)CCl AQFDXZOGFHBNRW-UHFFFAOYSA-N 0.000 description 1
KJHYAEZMOHLVCH-UHFFFAOYSA-N 2-ethyl-1-benzofuran Chemical compound C1=CC=C2OC(CC)=CC2=C1 KJHYAEZMOHLVCH-UHFFFAOYSA-N 0.000 description 1
PGHBDULKXIGKRN-UHFFFAOYSA-N 3-(chloromethyl)-2-propan-2-yl-1-benzofuran Chemical compound C(C)(C)C=1OC2=C(C1CCl)C=CC=C2 PGHBDULKXIGKRN-UHFFFAOYSA-N 0.000 description 1
MYKCEOXLNCJESE-UHFFFAOYSA-N 3-(chloromethyl)-2-propyl-1-benzofuran Chemical compound C(CC)C1=C(C2=C(O1)C=CC=C2)CCl MYKCEOXLNCJESE-UHFFFAOYSA-N 0.000 description 1
SNDPDIKRADZYGK-UHFFFAOYSA-N 4,5-dihydro-1h-imidazol-1-ium;bromide Chemical compound Br.C1CN=CN1 SNDPDIKRADZYGK-UHFFFAOYSA-N 0.000 description 1
IFCOMSZHIDTXOT-UHFFFAOYSA-N 4,5-dihydro-1h-imidazole;sulfuric acid Chemical compound C1CN=CN1.OS(O)(=O)=O IFCOMSZHIDTXOT-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
241000700198 Cavia Species 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
GLNADSQYFUSGOU-GPTZEZBUSA-J Trypan blue Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(/N=N/C3=CC=C(C=C3C)C=3C=C(C(=CC=3)\N=N\C=3C(=CC4=CC(=CC(N)=C4C=3O)S([O-])(=O)=O)S([O-])(=O)=O)C)=C(O)C2=C1N GLNADSQYFUSGOU-GPTZEZBUSA-J 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 1
229960001950 benzethonium chloride Drugs 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
230000008602 contraction Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 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
239000005457 ice water Substances 0.000 description 1
230000002262 irrigation Effects 0.000 description 1
238000003973 irrigation Methods 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000010410 layer Substances 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
229910000160 potassium phosphate Inorganic materials 0.000 description 1
235000011009 potassium phosphates Nutrition 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
230000002035 prolonged effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO192/72A 1971-01-27 1972-01-26 NO134115C (nl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB332771		1971-01-27

Publications (2)

Publication Number	Publication Date
NO134115B true NO134115B (nl)	1976-05-10
NO134115C NO134115C (nl)	1976-08-18

Family

ID=9756227

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO192/72A NO134115C (nl)	1971-01-27	1972-01-26

Country Status (17)

Country	Link
US (1)	US3818035A (nl)
JP (1)	JPS4938273B1 (nl)
AT (1)	AT311336B (nl)
BE (1)	BE777689A (nl)
CA (1)	CA962273A (nl)
CH (1)	CH535254A (nl)
DE (1)	DE2203373C3 (nl)
DK (1)	DK138496B (nl)
FI (1)	FI55841C (nl)
GB (1)	GB1333471A (nl)
HU (1)	HU162823B (nl)
NL (1)	NL150454B (nl)
NO (1)	NO134115C (nl)
SE (1)	SE378426B (nl)
SU (1)	SU474145A3 (nl)
YU (1)	YU34694B (nl)
ZA (1)	ZA72286B (nl)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3927023A (en) *	1974-05-24	1975-12-16	Warner Lambert Co	Imidazolyl benzofurans
DE3049542A1 (de) *	1980-12-31	1982-07-29	Basf Ag, 6700 Ludwigshafen	Azolylalkyl-2,3-dihydrobenzofurane, diese enthaltende fungizide und verfahren zu ihrer herstellung
ZA825413B (en) *	1981-08-26	1983-06-29	Pfizer	Thromboxane synthetase inhibitors, processes for their production, and pharmaceutical compositions comprising them
US4851554A (en) *	1987-04-06	1989-07-25	University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4806663A (en) *	1987-04-06	1989-02-21	The University Of Tennessee Research Corporation	Certain 3-substituted 2-alkyl benzofuran derivatives
US4831156A (en) *	1987-09-30	1989-05-16	The University Of Tennessee Research Corp.	3-substituted 2-alkyl indole derivatives
DK0924209T3 (da) *	1997-12-19	2003-08-25	Lilly Co Eli	Hypoglykæmiske imidazolinforbindelser
US7777035B2 (en) *	2005-06-22	2010-08-17	Chemocentryx, Inc.	Azaindazole compounds and methods of use
JP2009524617A (ja) *	2006-01-27	2009-07-02	エフ．ホフマン−ラロシュアーゲー	置換２−イミダゾール又はイミダゾリン誘導体の使用
KR101176699B1 (ko) *	2006-10-19	2012-08-23	에프. 호프만-라 로슈 아게	아미노메틸-4-이미다졸
KR101172940B1 (ko) *	2006-10-19	2012-08-10	에프. 호프만-라 로슈 아게	트레이스 아민 관련 수용체에 대해 친화도를 갖는 아미노메틸-2-이미다졸
ATE533755T1 (de) *	2006-11-02	2011-12-15	Hoffmann La Roche	Substituierte 2-imidazole als modulatoren der mit spurenaminen assoziierten rezeptoren
RU2456281C2 (ru) *	2006-11-16	2012-07-20	Ф. Хоффманн-Ля Рош Аг	Замещенные 4-имидазолы, способ их получения и их применение
BRPI0720047A2 (pt) *	2006-12-13	2013-12-24	Hoffmann La Roche	2-imidazóis como ligantes para receptores associados a aminas de traço (taar)
US20080146523A1 (en) *	2006-12-18	2008-06-19	Guido Galley	Imidazole derivatives
CA2675221C (en) *	2007-02-02	2016-02-23	F. Hoffmann-La Roche Ag	Novel 2-aminooxazolines as taar1 ligands
KR101222412B1 (ko) *	2007-02-15	2013-01-15	에프. 호프만-라 로슈 아게	Ｔａａｒ1 리간드로서의 2-아미노옥사졸린
WO2009003868A2 (en)	2007-07-02	2009-01-08	F. Hoffmann-La Roche Ag	2 -imidazolines having a good affinity to the trace amine associated receptors (taars)
CA2691704A1 (en) *	2007-07-03	2009-01-08	F. Hoffmann-La Roche Ag	4-imidazolines and their use as antidepressants
BRPI0813837A2 (pt) *	2007-07-27	2015-01-06	Hoffmann La Roche	2-azetidinametanoaminas e 2-pirrolidinametanoaminas como ligantes de taar
WO2009016088A1 (en) *	2007-08-02	2009-02-05	F. Hoffmann-La Roche Ag	The use of benzamide derivatives for the treatment of cns disorders
JP5341084B2 (ja) *	2007-08-03	2013-11-13	エフ．ホフマン−ラロシュアーゲー	Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体
US8242153B2 (en) *	2008-07-24	2012-08-14	Hoffmann-La Roche Inc.	4,5-dihydro-oxazol-2YL derivatives
RU2513086C2 (ru) *	2008-07-24	2014-04-20	Ф.Хоффманн-Ля Рош Аг	Производные 4,5-дигидро-оксазол-2-ила
US20100311798A1 (en) *	2009-06-05	2010-12-09	Decoret Guillaume	2-aminooxazolines as taar1 ligands
US8354441B2 (en) *	2009-11-11	2013-01-15	Hoffmann-La Roche Inc.	Oxazoline derivatives
US9452980B2 (en)	2009-12-22	2016-09-27	Hoffmann-La Roche Inc.	Substituted benzamides
AU2017234042B2 (en)	2016-03-17	2020-11-19	F. Hoffmann-La Roche Ag	5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of TAAR

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1121054B (de) *	1960-11-23	1962-01-04	Merck Ag E	Verfahren zur Herstellung eines neuen Imidazolinderivates und dessen Saeureadditionssalzen

1971
- 1971-01-27 GB GB332771A patent/GB1333471A/en not_active Expired
1972
- 1972-01-05 BE BE777689A patent/BE777689A/xx not_active IP Right Cessation
- 1972-01-06 CH CH17272A patent/CH535254A/fr not_active IP Right Cessation
- 1972-01-10 US US00216795A patent/US3818035A/en not_active Expired - Lifetime
- 1972-01-17 ZA ZA720286A patent/ZA72286B/xx unknown
- 1972-01-25 DE DE2203373A patent/DE2203373C3/de not_active Expired
- 1972-01-26 HU HULA791A patent/HU162823B/hu not_active IP Right Cessation
- 1972-01-26 YU YU181/72A patent/YU34694B/xx unknown
- 1972-01-26 DK DK34572AA patent/DK138496B/da unknown
- 1972-01-26 SE SE7200867A patent/SE378426B/xx unknown
- 1972-01-26 NO NO192/72A patent/NO134115C/no unknown
- 1972-01-27 SU SU1742351A patent/SU474145A3/ru active
- 1972-01-27 AT AT64772A patent/AT311336B/de not_active IP Right Cessation
- 1972-01-27 CA CA133,337A patent/CA962273A/en not_active Expired
- 1972-01-27 JP JP47010207A patent/JPS4938273B1/ja active Pending
- 1972-01-27 NL NL727201121A patent/NL150454B/nl not_active IP Right Cessation
- 1972-01-27 FI FI219/72A patent/FI55841C/fi active

Also Published As

Publication number	Publication date
NL7201121A (nl)	1972-07-31
DE2203373B2 (de)	1977-08-11
AT311336B (de)	1973-11-12
JPS4938273B1 (nl)	1974-10-16
NO134115C (nl)	1976-08-18
AU3817772A (en)	1973-07-26
HU162823B (nl)	1973-04-28
GB1333471A (en)	1973-10-10
BE777689A (fr)	1972-07-05
US3818035A (en)	1974-06-18
SE378426B (nl)	1975-09-01
DK138496C (nl)	1979-02-26
DE2203373A1 (de)	1972-08-17
CA962273A (en)	1975-02-04
ZA72286B (en)	1972-09-27
CH535254A (fr)	1973-03-31
FI55841C (fi)	1979-10-10
FI55841B (fi)	1979-06-29
YU18172A (en)	1979-07-10
NL150454B (nl)	1976-08-16
DE2203373C3 (de)	1978-04-13
SU474145A3 (ru)	1975-06-14
DK138496B (da)	1978-09-18
YU34694B (en)	1979-12-31

Publication	Publication Date	Title
NO134115B (nl)	1976-05-10
EP0201735B1 (de)	1990-09-12	N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung
FR2513250A1 (fr)	1983-03-25	Nouvelles cyclobutene-3,4-diones substituees
KR20090015912A (ko)	2009-02-12	Ｃ－글리코시드 유도체와 ｌ－프롤린과의 공결정
JPS6253504B2 (nl)	1987-11-10
NZ232258A (en)	1991-06-25	1-benzyl-indazol-3-yl methoxy acetic acid derivatives; preparatory processes pharmaceutical compositions and intermediates
JPS6343386B2 (nl)	1988-08-30
JP3857429B2 (ja)	2006-12-13	含硫黄抗真菌剤
DK160760B (da)	1991-04-15	Analogifremgangsmaade til fremstilling af n-naphthoylglycinderivater
RU2264382C1 (ru)	2005-11-20	Новые фенилэтаноламиновые соединения в качестве агонистов и бета2-рецептора и способ их получения
NO140348B (no)	1979-05-07	Analogifremgangsmaate til fremstilling av nye terapeutisk aktive 3-(amino-2-hydroksypropoksy)-isoindolin-1-on-forbindelser
JPH01106839A (ja)	1989-04-24	アルカジエン誘導体類、それらの製造、およびそれらを含有している薬学的組成物
DE3785104T2 (de)	1993-09-02	Pharmazeutisch nuetzliche thiazolidin-4-karbonsaeure-derivate.
DE2511647A1 (de)	1975-09-25	Neue benzopyranderivate
FI98519C (fi)	1997-07-10	Menetelmä substituoitujen indolien valmistamiseksi
JPH0819058B2 (ja)	1996-02-28	新規置換アミン化合物およびその製造方法
KR20010024074A (ko)	2001-03-26	이미다졸린 화합물
WO2023272571A1 (zh)	2023-01-05	2,3-环氧丁二酰衍生物的医药用途
NO141555B (no)	1979-12-27	Analogifremgangsmaate for fremstilling av nye terapeutisk virksomme dibenzocykloheptenkarboksamider
KR870001239B1 (ko)	1987-06-26	테트라하이드로-β-카르보린 유도체의 제조방법
NO138804B (no)	1978-08-07	Analogifremgangsmaater til fremstilling av aminosyrederivater med antidepressiv virkning
EP0000693A1 (de)	1979-02-21	Aminophenoxymethyl-2-morpholinderivate, ihre Herstellung und sie enthaltende Arzneimittel
EP0371342B1 (de)	1994-12-14	2-Halogensubstituierte N-Indolylethyl-sulfonsäureamide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DD258812A1 (de)	1988-08-03	Verfahren zur herstellung neuer ixoxazolderivate
JPS6229428B2 (nl)	1987-06-25