NO123430B - - Google Patents
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- Publication number
- NO123430B NO123430B NO4649/69A NO464969A NO123430B NO 123430 B NO123430 B NO 123430B NO 4649/69 A NO4649/69 A NO 4649/69A NO 464969 A NO464969 A NO 464969A NO 123430 B NO123430 B NO 123430B
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydro
- quinazolin
- dimethyl
- lower alkyl
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 2
- 229960004217 benzyl alcohol Drugs 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- -1 alkyl radicals Chemical class 0.000 description 16
- 239000007858 starting material Substances 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 150000003246 quinazolines Chemical class 0.000 description 5
- QAENFGLSHOAYSC-UHFFFAOYSA-N 4,4-dimethyl-1,3-dihydroquinazolin-2-one Chemical compound C1=CC=C2C(C)(C)NC(=O)NC2=C1 QAENFGLSHOAYSC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 230000000994 depressogenic effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- UZXREFASOUJZAS-UHFFFAOYSA-N 2-(2-aminophenyl)propan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1N UZXREFASOUJZAS-UHFFFAOYSA-N 0.000 description 2
- OJBCNOBBJUMWBQ-UHFFFAOYSA-N 3-(2-aminophenyl)pentan-3-ol Chemical compound CCC(O)(CC)C1=CC=CC=C1N OJBCNOBBJUMWBQ-UHFFFAOYSA-N 0.000 description 2
- YESQKSTUCWKJKE-UHFFFAOYSA-N 4,4-dimethyl-1,3-dihydroquinazoline-2-thione Chemical compound CC1(NC(NC2=CC=CC=C12)=S)C YESQKSTUCWKJKE-UHFFFAOYSA-N 0.000 description 2
- XSVNODGGUOZJSE-UHFFFAOYSA-N CC1(NC(NC2=C(C=C(C=C12)Cl)Cl)=O)C Chemical compound CC1(NC(NC2=C(C=C(C=C12)Cl)Cl)=O)C XSVNODGGUOZJSE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229960004815 meprobamate Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- OEIYYMRYDAAANK-UHFFFAOYSA-N 2-(2-amino-3,5-dibromophenyl)propan-2-ol Chemical compound NC1=C(C=C(C=C1Br)Br)C(O)(C)C OEIYYMRYDAAANK-UHFFFAOYSA-N 0.000 description 1
- ORNPWEUCSKIEJX-UHFFFAOYSA-N 2-(2-amino-3,5-dichlorophenyl)propan-2-ol Chemical compound CC(C)(O)C1=CC(Cl)=CC(Cl)=C1N ORNPWEUCSKIEJX-UHFFFAOYSA-N 0.000 description 1
- LTXRKVHNRDEBRT-UHFFFAOYSA-N 2-(2-amino-5-bromophenyl)propan-2-ol Chemical compound CC(C)(O)C1=CC(Br)=CC=C1N LTXRKVHNRDEBRT-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- QRYRATKXCRCOCA-UHFFFAOYSA-N NC1=C(C=C(C=C1)Cl)C(O)(C)C Chemical compound NC1=C(C=C(C=C1)Cl)C(O)(C)C QRYRATKXCRCOCA-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2416068 | 1968-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123430B true NO123430B (de) | 1971-11-15 |
Family
ID=11212294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4649/69A NO123430B (de) | 1968-11-26 | 1969-11-24 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3660322A (de) |
| AT (1) | AT290542B (de) |
| BE (1) | BE742205A (de) |
| BR (1) | BR6914433D0 (de) |
| CH (1) | CH523892A (de) |
| DE (1) | DE1958515B2 (de) |
| DK (1) | DK123239B (de) |
| ES (1) | ES373909A1 (de) |
| FR (1) | FR2024241B1 (de) |
| GB (1) | GB1231959A (de) |
| IE (1) | IE33406B1 (de) |
| IL (1) | IL33393A (de) |
| NL (1) | NL147140B (de) |
| NO (1) | NO123430B (de) |
| SE (1) | SE360659B (de) |
| YU (1) | YU33286B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE31617E (en) * | 1972-02-04 | 1984-06-26 | Bristol-Myers Company | Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones |
| DE3815767A1 (de) * | 1988-05-09 | 1989-11-23 | Karl Niggemeier | Abhefter fuer einzelblaetter |
| WO1993022292A1 (en) * | 1992-05-07 | 1993-11-11 | Merck & Co., Inc. | New quinazolines as inhibitors of hiv reverse transcriptase |
| US6124302A (en) * | 1997-04-09 | 2000-09-26 | Dupont Pharmaceuticals | 4,4-disubstituted-3,4-dihydro-2(1H)-quinazolinones useful as HIV reverse transcriptase inhibitors |
| WO1999050253A1 (en) * | 1998-03-27 | 1999-10-07 | Du Pont Pharmaceuticals Company | 4,4-disubstituted-3,4-dihydro-2(1h)-quinazolinthione derivatives, their preparation and their use as hiv reverse transcriptase inhibitors |
-
1969
- 1969-11-13 NL NL696917085A patent/NL147140B/xx unknown
- 1969-11-21 DE DE19691958515 patent/DE1958515B2/de active Granted
- 1969-11-21 IE IE1581/69A patent/IE33406B1/xx unknown
- 1969-11-21 IL IL33393A patent/IL33393A/en unknown
- 1969-11-21 YU YU2922/69A patent/YU33286B/xx unknown
- 1969-11-21 FR FR696940093A patent/FR2024241B1/fr not_active Expired
- 1969-11-21 US US878880A patent/US3660322A/en not_active Expired - Lifetime
- 1969-11-21 AT AT1088169A patent/AT290542B/de not_active IP Right Cessation
- 1969-11-24 GB GB1231959D patent/GB1231959A/en not_active Expired
- 1969-11-24 NO NO4649/69A patent/NO123430B/no unknown
- 1969-11-24 BR BR214433/69A patent/BR6914433D0/pt unknown
- 1969-11-24 SE SE16089/69A patent/SE360659B/xx unknown
- 1969-11-24 DK DK621469AA patent/DK123239B/da unknown
- 1969-11-25 ES ES373909A patent/ES373909A1/es not_active Expired
- 1969-11-25 CH CH1754469A patent/CH523892A/de not_active IP Right Cessation
- 1969-11-25 BE BE742205D patent/BE742205A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1958515A1 (de) | 1970-07-09 |
| YU292269A (en) | 1976-03-31 |
| DE1958515B2 (de) | 1976-06-24 |
| YU33286B (en) | 1976-08-31 |
| CH523892A (de) | 1972-06-15 |
| IE33406L (en) | 1970-05-26 |
| IE33406B1 (en) | 1974-06-12 |
| FR2024241B1 (de) | 1973-07-13 |
| ES373909A1 (es) | 1972-08-16 |
| GB1231959A (de) | 1971-05-12 |
| IL33393A0 (en) | 1970-01-29 |
| NL147140B (nl) | 1975-09-15 |
| BE742205A (de) | 1970-05-25 |
| DK123239B (da) | 1972-05-29 |
| SE360659B (de) | 1973-10-01 |
| IL33393A (en) | 1973-04-30 |
| NL6917085A (de) | 1970-05-28 |
| BR6914433D0 (pt) | 1973-02-22 |
| US3660322A (en) | 1972-05-02 |
| AT290542B (de) | 1971-06-11 |
| FR2024241A1 (de) | 1970-08-28 |
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