NL8004668A - 2-(pyridyl-cyclopropyl)chromonderivaten, alsmede werkwijzen ter bereiding ervan en farmaceutische preparaten. - Google Patents

2-(pyridyl-cyclopropyl)chromonderivaten, alsmede werkwijzen ter bereiding ervan en farmaceutische preparaten. Download PDF

Info

Publication number: NL8004668A
Authority: NL; Netherlands
Prior art keywords: pyridyl; cyclopropyl; methyl; formula; trans
Prior art date: 1979-10-26

Application number

NL8004668A

Other languages

English (en)

Dutch (nl)

Original Assignee

Erba Farmitalia

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.)

1979-10-26

Filing date

1980-08-18

Publication date

1981-04-28

1980-08-18 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1981-04-28 Publication of NL8004668A publication Critical patent/NL8004668A/nl

Links

238000000034 method Methods 0.000 title claims description 15
239000000825 pharmaceutical preparation Substances 0.000 title claims description 7
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical class [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 55
-1 6-methyl-2-pyridyl Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
VSPPROBMTZRYRB-UHFFFAOYSA-N 2-(1-pyridin-2-ylcyclopropyl)chromen-4-one Chemical class O1C2=CC=CC=C2C(=O)C=C1C1(C=2N=CC=CC=2)CC1 VSPPROBMTZRYRB-UHFFFAOYSA-N 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 4
159000000000 sodium salts Chemical class 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
150000004777 chromones Chemical class 0.000 claims description 3
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 3
125000004185 ester group Chemical group 0.000 claims 1
125000004494 ethyl ester group Chemical class 0.000 claims 1
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SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
239000007888 film coating Substances 0.000 description 1
238000009501 film coating Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 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
208000015181 infectious disease Diseases 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000010354 integration Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
VKQFZTYQLVVTJE-ZRDIBKRKSA-N methyl 2-[(E)-2-(6-methylpyridin-2-yl)ethenyl]-4-oxo-3-propylchromene-6-carboxylate Chemical compound COC(=O)C=1C=C2C(C(=C(OC2=CC=1)\C=C\C1=NC(=CC=C1)C)CCC)=O VKQFZTYQLVVTJE-ZRDIBKRKSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002736 nonionic surfactant Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 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
239000003921 oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229940068965 polysorbates Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940032147 starch Drugs 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000009495 sugar coating Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
231100000048 toxicity data Toxicity 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
YRYSAWZMIRQUBO-UHFFFAOYSA-N trimethylsulfoxonium Chemical compound C[S+](C)(C)=O YRYSAWZMIRQUBO-UHFFFAOYSA-N 0.000 description 1
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- 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
- C07D405/08—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 alicyclic rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NL8004668A 1979-10-26 1980-08-18 2-(pyridyl-cyclopropyl)chromonderivaten, alsmede werkwijzen ter bereiding ervan en farmaceutische preparaten. NL8004668A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7937200		1979-10-26
GB7937200		1979-10-26

Publications (1)

Publication Number	Publication Date
NL8004668A true NL8004668A (nl)	1981-04-28

Family

ID=10508789

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8004668A NL8004668A (nl)	1979-10-26	1980-08-18	2-(pyridyl-cyclopropyl)chromonderivaten, alsmede werkwijzen ter bereiding ervan en farmaceutische preparaten.

Country Status (8)

Country	Link
US (1)	US4310589A (fr)
BE (1)	BE885318R (fr)
CA (1)	CA1154772A (fr)
FR (1)	FR2468604A2 (fr)
GR (1)	GR70216B (fr)
NL (1)	NL8004668A (fr)
PH (1)	PH18736A (fr)
ZA (1)	ZA804788B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20150118158A (ko) *	2013-02-22	2015-10-21	머크 샤프 앤드 돔 코포레이션	항당뇨병 비시클릭 화합물

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA781467A (en)		1968-03-26	Fitzmaurice Colin	Furochromone derivatives
US3816466A (en) *	1971-12-22	1974-06-11	Warner Lambert Co	Flavanoid ring systems
JPS5118955B2 (fr) *	1972-04-12	1976-06-14
US3993669A (en) *	1974-06-05	1976-11-23	Syntex (U.S.A.) Inc.	Mono- and disubstituted 1.4-benzopyrone-6-carboxylic acids and derivatives thereof
US4157334A (en) *	1974-12-26	1979-06-05	Carlo Erba S. P. A.	6-Carboxy-flavone derivatives and process for their preparation
US4033845A (en) *	1975-11-20	1977-07-05	Warner-Lambert Company	[2-(4-Oxo-4H-1-benzopyran-2-yl)ethenyl]benzonitriles and benzoic acids
US4018798A (en) *	1975-11-20	1977-04-19	Warner-Lambert Company	Substituted (4-oxo-4H-1-benzopyran-2-yl)cyclopropane carboxylic acids and esters
AU508350B2 (en) *	1976-06-16	1980-03-20	Farmitalia Carlo Erba S.P.A.	Substicuted 2-vinyl-chromones
US4143145A (en) *	1977-01-12	1979-03-06	Carlo Erba S. P. A.	Substituted 2-vinyl-chromones and process for their preparation
GB1544049A (en) *	1977-06-08	1979-04-11	Erba Carlo Spa	Substituted 2-vinyl-chromones
US4160028A (en) *	1977-08-02	1979-07-03	Carlo Erba S.P.A.	Substituted 2-cyclopropyl-chromones and pharmaceutical compositions and use thereof

1980
- 1980-08-06 ZA ZA00804788A patent/ZA804788B/xx unknown
- 1980-08-18 NL NL8004668A patent/NL8004668A/nl not_active Application Discontinuation
- 1980-09-03 PH PH24532A patent/PH18736A/en unknown
- 1980-09-12 US US06/186,544 patent/US4310589A/en not_active Expired - Lifetime
- 1980-09-19 BE BE0/202173A patent/BE885318R/fr active
- 1980-09-29 CA CA000361220A patent/CA1154772A/fr not_active Expired
- 1980-09-29 FR FR8020821A patent/FR2468604A2/fr active Granted
- 1980-09-30 GR GR62996A patent/GR70216B/el unknown

Also Published As

Publication number	Publication date
CA1154772A (fr)	1983-10-04
US4310589A (en)	1982-01-12
FR2468604A2 (fr)	1981-05-08
GR70216B (fr)	1982-08-31
FR2468604B2 (fr)	1983-11-18
PH18736A (en)	1985-09-16
BE885318R (fr)	1981-03-19
ZA804788B (en)	1981-07-29

Legal Events

Date	Code	Title
1981-05-11	A1A	A request for search or an international-type search has been filed
1982-02-01	BB	A search report has been drawn up
1985-01-01	A85	Still pending on 85-01-01
1987-08-03	BC	A request for examination has been filed
1991-04-02	BV	The patent application has lapsed

Publication	Publication Date	Title
AU683151B2 (en)	1997-10-30	Novel N-pyridyl carboxamides and derivatives, processes for their preparation and the pharmaceutical compositions which contain them
JPH072770A (ja)	1995-01-06	新規な置換インドール類、その製造法及びそのインドール類を含有する製剤組成物
NO173444B (no)	1993-09-06	Analogifremgangsmaate til fremstilling av terapeutisk aktive 4-(4'-fluorfenyl-)-tienopyridin-derivater
JPH066576B2 (ja)	1994-01-26	アミノキノリン誘導体及びその製法
EP0053789B1 (fr)	1985-03-27	Dérivés de 2-pyridinecarboxamide, leur procédé de préparation et une composition pharmaceutique utilisable comme agent anti-allergique
AT371461B (de)	1983-06-27	Verfahren zur herstellung neuer benzopyranderivate und deren salze
JPS60156676A (ja)	1985-08-16	新規ベンズイミダゾ−ル
NL8004668A (nl)	1981-04-28	2-(pyridyl-cyclopropyl)chromonderivaten, alsmede werkwijzen ter bereiding ervan en farmaceutische preparaten.
NL8002656A (nl)	1980-11-11	Gesubstitueerde pyrido 1.2-a pyrimidinen.
JP2009541410A5 (fr)	2010-07-22
US4157334A (en)	1979-06-05	6-Carboxy-flavone derivatives and process for their preparation
FI72516B (fi)	1987-02-27	Foerfarande foer framstaellning av farmaceutiskt aktiva 3,6-disubstituerade 2-cyklopropyl-kromoner.
FI71733B (fi)	1986-10-31	Foerfarande foer framstaellning av farmaceutiskt aktiva 3,6-substituerade 2-vinyl-kromoner
SU957766A3 (ru)	1982-09-07	Способ получени замещенных 2-циклопропилхромонов или их солей
GB1593645A (en)	1981-07-22	Carbocyclic fused thiophen-2-oxaminic acid derivatives
Nardi et al.	1975	Heterocyclic compounds from 3, 3‐dimercapto‐1‐aryl‐2‐propen‐1‐ones. Note 2. Condensation with o‐aminothophenol and o‐aminophenol
US4183945A (en)	1980-01-15	Substituted 2-vinyl-chromones and process for their preparation
HU190945B (en)	1986-12-28	Process for preparing substituted thiazolo/3,2-a/pyrimidine-carb oxylic acid derivatives
KR820000370B1 (ko)	1982-03-25	치환된 2-사이클로프로필-크로몬의 제조방법
US4598090A (en)	1986-07-01	Condensed benzopyrone derivatives
KR820000214B1 (ko)	1982-03-05	치환된 2-사이클로프로필-크로몬의 제조방법
US4183946A (en)	1980-01-15	Substituted 2-vinyl-chromones and process for their preparation
GB2061261A (en)	1981-05-13	Substituted 2-(pyridylcyclopropyl)-chromones
DE3036553A1 (de)	1981-05-07	Substituierte 2-(pyridyl-cyclopropyl)chromone, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
CS207642B2 (cs)	1981-08-31	Způsob výroby substituovaných 2-cyldopropyIchromonů