NO132760B - - Google Patents

Download PDF

Info

Publication number: NO132760B
Authority: NO; Norway
Prior art keywords: lower alkyl; phenyl; pyrimidin; general formula; hydrogen
Prior art date: 1970-08-14

Application number

NO3028/71A

Other languages

English (en)

Norwegian (no)

Other versions

NO132760C (fr

Inventor

J L E Baetz

Original Assignee

Seperic

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.)

1970-08-14

Filing date

1971-08-13

Publication date

1975-09-22

1971-08-13 Application filed by Seperic filed Critical Seperic

1975-09-22 Publication of NO132760B publication Critical patent/NO132760B/no

1975-12-29 Publication of NO132760C publication Critical patent/NO132760C/no

Links

150000001875 compounds Chemical class 0.000 claims description 17
REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
239000008096 xylene Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000243 solution Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SILRNKZBMNSABG-UHFFFAOYSA-N 4-methyl-4,5-dihydro-1,3-thiazol-2-amine Chemical compound CC1CSC(N)=N1 SILRNKZBMNSABG-UHFFFAOYSA-N 0.000 description 1
BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000282941 Rangifer tarandus Species 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
UVRHPZOOCXESOY-UHFFFAOYSA-N pyrimidine;1,3-thiazole Chemical class C1=CSC=N1.C1=CN=CN=C1 UVRHPZOOCXESOY-UHFFFAOYSA-N 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Thiazole And Isothizaole Compounds (AREA)

NO3028/71A 1970-08-14 1971-08-13 NO132760C (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB3918970		1970-08-14

Publications (2)

Publication Number	Publication Date
NO132760B true NO132760B (fr)	1975-09-22
NO132760C NO132760C (fr)	1975-12-29

Family

ID=10408188

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO3028/71A NO132760C (fr)	1970-08-14	1971-08-13

Country Status (21)

Country	Link
JP (1)	JPS5116437B1 (fr)
AT (1)	AT305279B (fr)
AU (1)	AU3231071A (fr)
BE (1)	BE770873A (fr)
CA (1)	CA925868A (fr)
CH (1)	CH542231A (fr)
DE (1)	DE2140601C3 (fr)
DK (1)	DK129718B (fr)
ES (1)	ES394727A1 (fr)
FI (1)	FI52096C (fr)
FR (1)	FR2102254B1 (fr)
GB (1)	GB1306558A (fr)
IE (1)	IE35491B1 (fr)
IL (1)	IL37431A (fr)
IS (1)	IS918B6 (fr)
LU (1)	LU63700A1 (fr)
NL (2)	NL149177B (fr)
NO (1)	NO132760C (fr)
OA (1)	OA03905A (fr)
SE (1)	SE380271B (fr)
ZA (1)	ZA715194B (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PL129612B1 (en) *	1980-07-24	1984-05-31	Rhone Poulenc Ind	Process for preparing novel derivatives of 2,3,6,7-tetrahydrothiazole/3,2-a/pirymidin-5-one
US4443451A (en) *	1981-07-15	1984-04-17	Janssen Pharmaceutica N.V.	Bicyclic pyrimidin-5-one derivatives
JPS5980072U (ja) *	1982-11-19	1984-05-30	株式会社東洋製作所	倉庫の扉開閉装置
JPS6354797U (fr) *	1986-09-29	1988-04-12

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1275804A (en) *	1969-07-03	1972-05-24	Seperic	Improvements in or relating to new sulphur containing derivatives of pyrimidine, their preparation and their applications

1970
- 1970-08-14 GB GB3918970A patent/GB1306558A/en not_active Expired
1971
- 1971-07-08 FR FR7125051A patent/FR2102254B1/fr not_active Expired
- 1971-08-03 IS IS2024A patent/IS918B6/is unknown
- 1971-08-03 IL IL37431A patent/IL37431A/en unknown
- 1971-08-03 BE BE770873A patent/BE770873A/fr unknown
- 1971-08-04 IE IE986/71A patent/IE35491B1/xx unknown
- 1971-08-04 ZA ZA715194A patent/ZA715194B/xx unknown
- 1971-08-05 CH CH1155771A patent/CH542231A/fr not_active IP Right Cessation
- 1971-08-05 SE SE7110021A patent/SE380271B/xx unknown
- 1971-08-09 OA OA54327A patent/OA03905A/fr unknown
- 1971-08-11 FI FI712245A patent/FI52096C/fi active
- 1971-08-11 LU LU63700D patent/LU63700A1/xx unknown
- 1971-08-12 AU AU32310/71A patent/AU3231071A/en not_active Expired
- 1971-08-12 ES ES394727A patent/ES394727A1/es not_active Expired
- 1971-08-13 AT AT711771A patent/AT305279B/de active
- 1971-08-13 NL NL717111222A patent/NL149177B/xx not_active IP Right Cessation
- 1971-08-13 DE DE2140601A patent/DE2140601C3/de not_active Expired
- 1971-08-13 DK DK398471AA patent/DK129718B/da unknown
- 1971-08-13 CA CA120534A patent/CA925868A/en not_active Expired
- 1971-08-13 NO NO3028/71A patent/NO132760C/no unknown
- 1971-08-13 JP JP46061591A patent/JPS5116437B1/ja active Pending
1976
- 1976-01-28 NL NL7600885A patent/NL7600885A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
NL149177B (nl)	1976-04-15
DK129718C (fr)	1975-04-28
JPS5116437B1 (fr)	1976-05-24
ZA715194B (en)	1972-04-26
NL7111222A (fr)	1972-02-16
IL37431A (en)	1974-10-22
CH542231A (fr)	1973-09-30
IS918B6 (is)	1975-12-24
IL37431A0 (en)	1971-11-29
IE35491B1 (en)	1976-03-03
IE35491L (en)	1972-02-14
AT305279B (de)	1973-02-26
GB1306558A (en)	1973-02-14
FR2102254A1 (fr)	1972-04-07
CA925868A (en)	1973-05-08
FI52096B (fr)	1977-02-28
IS2024A7 (is)	1972-02-15
BE770873A (fr)	1971-12-16
DE2140601A1 (de)	1972-02-17
SE380271B (sv)	1975-11-03
FR2102254B1 (fr)	1976-04-16
ES394727A1 (es)	1974-02-16
DE2140601C3 (de)	1975-02-13
DK129718B (da)	1974-11-11
NL7600885A (nl)	1976-04-29
NO132760C (fr)	1975-12-29
DE2140601B2 (de)	1974-05-30
LU63700A1 (fr)	1971-12-17
FI52096C (fi)	1977-06-10
OA03905A (fr)	1975-08-14
AU3231071A (en)	1973-02-15

Publication	Publication Date	Title
US4070368A (en)	1978-01-24	Process for preparing alkyl, aroyl substitute pyrrole-2-acetates
US4110337A (en)	1978-08-29	Triazolobenzodiazepines
HU198030B (en)	1989-07-28	Process for production of derivatives of benzotiasole and benzotiophen and medical preparatives containing these compounds as active substance
NO165841B (no)	1991-01-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive heteroaryl-3-okso-propannitril-derivater.
US3890347A (en)	1975-06-17	Isoindoline derivatives
Xu et al.	2017	Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
PL84191B1 (en)	1976-03-31	3-aroyl-alkenyleneimines[us3835149a]
IE42978B1 (en)	1980-11-19	Triaryl alkyl azabicyclo compounds
NO132760B (fr)	1975-09-22
NO791648L (no)	1979-11-20	Fremgangsmaate ved fremstilling av nye kinazolinderivater
NO127303B (fr)	1973-06-04
US4515944A (en)	1985-05-07	1,5-Diphenyl-2-haloalkylpyrazolin-3-one intermediates
US3888983A (en)	1975-06-10	Derivatives of thiazolino-pyrimidin-6-ones, in inducing analgesia
US3836541A (en)	1974-09-17	3-cyano-2-pyrryl oxamic acids
CS202079B2 (en)	1980-12-31	Method of producing novel derivatives of benzopyran
US3458515A (en)	1969-07-29	Piperazine substituted pyrroles
US3818090A (en)	1974-06-18	Novel quinolines in the treatment of pain and inflammation
NO164167B (no)	1990-05-28	Analogifremgangsmaate for fremstilling av derivater av 4-fenylkinazolin.
Patro et al.	2012	Synthesis and screening for antibacterial, analgesic and antiinflammatory activity of Mannich bases derived from 1H-indole-2, 3-dione
US4757070A (en)	1988-07-12	3-oxadiazolyl-5-aminoalkyl-beta-carboline derivatives compositions and use
NO830758L (no)	1983-09-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-fenyl-4,5,6,7-tetrahydro tieno (2,3-c) pyridin-derivater
US4420476A (en)	1983-12-13	Benzofuro[3,2-c]pyrazol-3-amine derivatives
US4136186A (en)	1979-01-23	Thieno[3,2-c]pyridine derivatives
NO139050B (no)	1978-09-18	Analogifremgangsmaate for fremstilling av terapeutisk aktive nororipavin- og tebainderivater
JPS6136754B2 (fr)	1986-08-20