NO127399B - - Google Patents
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- Publication number
- NO127399B NO127399B NO01138/70A NO113870A NO127399B NO 127399 B NO127399 B NO 127399B NO 01138/70 A NO01138/70 A NO 01138/70A NO 113870 A NO113870 A NO 113870A NO 127399 B NO127399 B NO 127399B
- Authority
- NO
- Norway
- Prior art keywords
- pyrazine
- urea
- ethyl
- amido
- carboxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000003216 pyrazines Chemical class 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000002425 crystallisation Methods 0.000 description 23
- 230000008025 crystallization Effects 0.000 description 23
- 239000002904 solvent Substances 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000004202 carbamide Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- HNFVMVJWZHNDNF-UHFFFAOYSA-N 5,6-dimethylpyrazine-2-carboxylic acid Chemical compound CC1=NC=C(C(O)=O)N=C1C HNFVMVJWZHNDNF-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- HSOOJEQQKCNYKJ-UHFFFAOYSA-N 3-chloro-5,6-dimethylpyrazine-2-carboxylic acid Chemical compound CC1=NC(Cl)=C(C(O)=O)N=C1C HSOOJEQQKCNYKJ-UHFFFAOYSA-N 0.000 description 2
- PMRPVXLESNMKLG-UHFFFAOYSA-N 3-chloropyrazine-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN=C1Cl PMRPVXLESNMKLG-UHFFFAOYSA-N 0.000 description 2
- HIQNMBCMDBUWJV-UHFFFAOYSA-N 3-methoxypyrazine-2-carboxylic acid Chemical compound COC1=NC=CN=C1C(O)=O HIQNMBCMDBUWJV-UHFFFAOYSA-N 0.000 description 2
- YVGVOPNUEFTVQO-UHFFFAOYSA-N 5-methoxypyrazine-2-carboxylic acid Chemical compound COC1=CN=C(C(O)=O)C=N1 YVGVOPNUEFTVQO-UHFFFAOYSA-N 0.000 description 2
- RBYJWCRKFLGNDB-UHFFFAOYSA-N 5-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=C(C(O)=O)C=N1 RBYJWCRKFLGNDB-UHFFFAOYSA-N 0.000 description 2
- KGGYMBKTQCLOTE-UHFFFAOYSA-N 6-chloropyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Cl)=N1 KGGYMBKTQCLOTE-UHFFFAOYSA-N 0.000 description 2
- RWGSCFHUIFPLEI-UHFFFAOYSA-N 6-methoxypyrazine-2-carboxylic acid Chemical compound COC1=CN=CC(C(O)=O)=N1 RWGSCFHUIFPLEI-UHFFFAOYSA-N 0.000 description 2
- YDSUJIRXXROKQG-UHFFFAOYSA-N 6-methylpyrazine-2-carboxylic acid Chemical compound CC1=CN=CC(C(O)=O)=N1 YDSUJIRXXROKQG-UHFFFAOYSA-N 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- AVGQTJUPLKNPQP-UHFFFAOYSA-N 1,1,1-trichloropropane Chemical compound CCC(Cl)(Cl)Cl AVGQTJUPLKNPQP-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YXABWCPPCNRFEJ-UHFFFAOYSA-N 3-amino-5,6-diphenylpyrazine-2-carboxylic acid Chemical compound C=1C=CC=CC=1C=1N=C(C(O)=O)C(N)=NC=1C1=CC=CC=C1 YXABWCPPCNRFEJ-UHFFFAOYSA-N 0.000 description 1
- NSBRFKAXSNUXQO-UHFFFAOYSA-N 3-aminopyrazine-2-carbohydrazide Chemical compound NNC(=O)C1=NC=CN=C1N NSBRFKAXSNUXQO-UHFFFAOYSA-N 0.000 description 1
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VPJDULFXCAQHRC-UHFFFAOYSA-N prop-2-enylurea Chemical compound NC(=O)NCC=C VPJDULFXCAQHRC-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1458169 | 1969-03-26 | ||
| IT1830169 | 1969-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127399B true NO127399B (nl) | 1973-06-18 |
Family
ID=26326731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01138/70A NO127399B (nl) | 1969-03-26 | 1970-03-25 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3669966A (nl) |
| BE (1) | BE747405A (nl) |
| CA (1) | CA952112A (nl) |
| CH (1) | CH547809A (nl) |
| CY (1) | CY645A (nl) |
| DE (1) | DE2012138C3 (nl) |
| DK (1) | DK128320B (nl) |
| FI (1) | FI52720C (nl) |
| FR (1) | FR2035890B1 (nl) |
| GB (1) | GB1249443A (nl) |
| IL (1) | IL34153A (nl) |
| MY (1) | MY7300007A (nl) |
| NL (1) | NL138933B (nl) |
| NO (1) | NO127399B (nl) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3320583A1 (de) * | 1983-06-08 | 1984-12-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue galenische zubereitungsformen von oralen antidiabetika und verfahren zu ihrer herstellung |
| DE3320582A1 (de) * | 1983-06-08 | 1984-12-13 | Dr. Karl Thomae Gmbh, 7950 Biberach | Gliquidonhaltige zubereitungsformen und verfahren zu ihrer herstellung |
| US5196410A (en) * | 1986-10-31 | 1993-03-23 | Pfizer Inc. | Transdermal flux enhancing compositions |
| US6361795B1 (en) | 1989-09-05 | 2002-03-26 | Alza Corporation | Method for lowering blood glucose |
| US5516906A (en) * | 1995-01-17 | 1996-05-14 | Usv Limited | Process for the preparation of N-[2-[4-(aminosulfonyl) phenyl]ethyl]5-methylpyrazinecarboxamide |
| US8236352B2 (en) * | 1998-10-01 | 2012-08-07 | Alkermes Pharma Ireland Limited | Glipizide compositions |
| US7041691B1 (en) * | 1999-06-30 | 2006-05-09 | Amgen Inc. | Compounds for the modulation of PPARγ activity |
| AU6118001A (en) * | 2000-05-03 | 2001-11-12 | Tularik Inc | Combination therapeutic compositions and methods of use |
| US20030171399A1 (en) * | 2000-06-28 | 2003-09-11 | Tularik Inc. | Quinolinyl and benzothiazolyl modulators |
| US8268352B2 (en) * | 2002-08-05 | 2012-09-18 | Torrent Pharmaceuticals Limited | Modified release composition for highly soluble drugs |
| US8216609B2 (en) * | 2002-08-05 | 2012-07-10 | Torrent Pharmaceuticals Limited | Modified release composition of highly soluble drugs |
| US7223761B2 (en) * | 2003-10-03 | 2007-05-29 | Amgen Inc. | Salts and polymorphs of a potent antidiabetic compound |
| US20070025953A1 (en) * | 2005-07-27 | 2007-02-01 | Jones Michael R | Co-therapy for diabetic conditions |
| CN104163864B (zh) * | 2007-03-30 | 2017-08-01 | Ambrx公司 | 经修饰fgf‑21多肽和其用途 |
| KR20240024362A (ko) | 2014-10-24 | 2024-02-23 | 브리스톨-마이어스 스큅 컴퍼니 | 변형된 fgf-21 폴리펩티드 및 그의 용도 |
| CN105399692A (zh) * | 2015-12-18 | 2016-03-16 | 四川大学 | 格列吡嗪晶型iii及其制备方法 |
| WO2018078657A1 (en) * | 2016-10-28 | 2018-05-03 | J.B. Chemicals & Pharmaceuticals Limited | Process for preparation of glipizide |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1185180B (de) * | 1963-10-19 | 1965-01-14 | Hoechst Ag | Verfahren zur Herstellung von Benzolsulfonylharnstoffen |
| NL6707184A (nl) * | 1966-06-06 | 1967-12-07 | ||
| US3573305A (en) * | 1968-12-30 | 1971-03-30 | Merck & Co Inc | (3-amino-pyrazinoyl)sulfamides and their preparation |
-
1969
- 1969-10-17 NL NL696915776A patent/NL138933B/nl not_active IP Right Cessation
-
1970
- 1970-02-20 FR FR7006139A patent/FR2035890B1/fr not_active Expired
- 1970-03-13 GB GB02321/70A patent/GB1249443A/en not_active Expired
- 1970-03-14 DE DE2012138A patent/DE2012138C3/de not_active Expired
- 1970-03-16 BE BE747405D patent/BE747405A/xx not_active IP Right Cessation
- 1970-03-20 FI FI700791A patent/FI52720C/fi active
- 1970-03-24 IL IL34153A patent/IL34153A/xx unknown
- 1970-03-24 US US22389A patent/US3669966A/en not_active Expired - Lifetime
- 1970-03-25 DK DK152570AA patent/DK128320B/da not_active IP Right Cessation
- 1970-03-25 CA CA078,355A patent/CA952112A/en not_active Expired
- 1970-03-25 NO NO01138/70A patent/NO127399B/no unknown
- 1970-03-25 CH CH454470A patent/CH547809A/xx not_active IP Right Cessation
-
1972
- 1972-06-16 CY CY64572A patent/CY645A/xx unknown
-
1973
- 1973-12-30 MY MY7/73A patent/MY7300007A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6915776A (nl) | 1970-09-29 |
| GB1249443A (en) | 1971-10-13 |
| IL34153A0 (en) | 1970-05-21 |
| US3669966A (en) | 1972-06-13 |
| CA952112A (en) | 1974-07-30 |
| IL34153A (en) | 1972-12-29 |
| DE2012138C3 (de) | 1978-08-10 |
| CH547809A (de) | 1974-04-11 |
| FR2035890B1 (nl) | 1974-01-11 |
| DK128320B (da) | 1974-04-08 |
| FI52720B (nl) | 1977-08-01 |
| FR2035890A1 (nl) | 1970-12-24 |
| DE2012138A1 (de) | 1970-10-01 |
| NL138933B (nl) | 1973-05-15 |
| FI52720C (fi) | 1977-11-10 |
| MY7300007A (en) | 1973-12-31 |
| BE747405A (fr) | 1970-08-31 |
| DE2012138B2 (de) | 1977-12-15 |
| CY645A (en) | 1972-06-16 |
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