PL91696B1 - - Google Patents
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- PL91696B1 PL91696B1 PL1974173196A PL17319674A PL91696B1 PL 91696 B1 PL91696 B1 PL 91696B1 PL 1974173196 A PL1974173196 A PL 1974173196A PL 17319674 A PL17319674 A PL 17319674A PL 91696 B1 PL91696 B1 PL 91696B1
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- PL
- Poland
- Prior art keywords
- methyl
- compound
- compounds
- column
- nitro
- Prior art date
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- 238000000034 method Methods 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- -1 1-methyl--5-nitro-2-imidazolyl Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
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- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 claims description 4
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- SAUUKWGLDNIFRT-UHFFFAOYSA-N 5-amino-1-(2-hydroxyethyl)-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NN(CCO)C(N)=C1C#N SAUUKWGLDNIFRT-UHFFFAOYSA-N 0.000 claims 1
- MHWJFZBIEQEJHB-UHFFFAOYSA-N 5-amino-1-ethyl-3-(1-methyl-5-nitroimidazol-2-yl)pyrazole-4-carbonitrile Chemical compound N#CC1=C(N)N(CC)N=C1C1=NC=C([N+]([O-])=O)N1C MHWJFZBIEQEJHB-UHFFFAOYSA-N 0.000 claims 1
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- 238000011161 development Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 1
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- 229940093500 ethoxyquin Drugs 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 1
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
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- 208000019423 liver disease Diseases 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
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- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- OWPQUQSVZURPSP-UHFFFAOYSA-N n-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]methanamine Chemical compound CNN=CC1=NC=C([N+]([O-])=O)N1C OWPQUQSVZURPSP-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
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- 239000007800 oxidant agent Substances 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940055726 pantothenic acid Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 208000008494 pericarditis Diseases 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- FFNMBRCFFADNAO-UHFFFAOYSA-N pirenzepine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 FFNMBRCFFADNAO-UHFFFAOYSA-N 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- UKPBXIFLSVLDPA-UHFFFAOYSA-N propylhydrazine Chemical compound CCCNN UKPBXIFLSVLDPA-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000019157 thiamine Nutrition 0.000 description 1
- KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 description 1
- 229960003495 thiamine Drugs 0.000 description 1
- 239000011721 thiamine Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- OECHMUONYSVUHV-UHFFFAOYSA-I tricalcium;carbonate;phosphate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C([O-])=O.[O-]P([O-])([O-])=O OECHMUONYSVUHV-UHFFFAOYSA-I 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical group 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38513673A | 1973-08-02 | 1973-08-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL91696B1 true PL91696B1 (en, 2012) | 1977-03-31 |
Family
ID=23520163
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974192766A PL96805B1 (pl) | 1973-08-02 | 1974-08-02 | Sposob wytwarzania nowych podstawionych pochodnych pirazolu |
| PL1974184214A PL94238B1 (en, 2012) | 1973-08-02 | 1974-08-02 | |
| PL1974184215A PL92429B1 (en, 2012) | 1973-08-02 | 1974-08-02 | |
| PL1974192765A PL96804B1 (pl) | 1973-08-02 | 1974-08-02 | Sposob wytwarzania nowych podstawionych pochodnych pirazolu |
| PL1974173196A PL91696B1 (en, 2012) | 1973-08-02 | 1974-08-02 |
Family Applications Before (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1974192766A PL96805B1 (pl) | 1973-08-02 | 1974-08-02 | Sposob wytwarzania nowych podstawionych pochodnych pirazolu |
| PL1974184214A PL94238B1 (en, 2012) | 1973-08-02 | 1974-08-02 | |
| PL1974184215A PL92429B1 (en, 2012) | 1973-08-02 | 1974-08-02 | |
| PL1974192765A PL96804B1 (pl) | 1973-08-02 | 1974-08-02 | Sposob wytwarzania nowych podstawionych pochodnych pirazolu |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5047978A (en, 2012) |
| AR (3) | AR203854A1 (en, 2012) |
| AT (1) | AT337691B (en, 2012) |
| BE (1) | BE818417A (en, 2012) |
| BR (1) | BR7406317D0 (en, 2012) |
| DD (1) | DD112759A5 (en, 2012) |
| DE (1) | DE2431775A1 (en, 2012) |
| DK (1) | DK410874A (en, 2012) |
| ES (1) | ES428914A0 (en, 2012) |
| FR (1) | FR2240009A1 (en, 2012) |
| IL (1) | IL45073A (en, 2012) |
| IT (1) | IT1049204B (en, 2012) |
| NL (1) | NL7410033A (en, 2012) |
| PL (5) | PL96805B1 (en, 2012) |
| RO (1) | RO63973A (en, 2012) |
| SE (1) | SE7409957L (en, 2012) |
| SU (2) | SU565630A3 (en, 2012) |
| ZA (1) | ZA743887B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6409055B2 (ja) * | 2013-05-20 | 2018-10-17 | ザ ユニバーシティ オブ ワシントン スルー イッツ センター フォー コマーシャライゼーションＴｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｗａｓｈｉｎｇｔｏｎ Ｔｈｒｏｕｇｈ Ｉｔｓ Ｃｅｎｔｅｒ Ｆｏｒ Ｃｏｍｍｅｒｃｉａｌｉｚａｔｉｏｎ | Ｃｄｐｋ１の５−アミノピラゾール−４−カルボキサミド阻害剤 |
-
1974
- 1974-06-18 ZA ZA00743887A patent/ZA743887B/xx unknown
- 1974-06-20 IL IL45073A patent/IL45073A/en unknown
- 1974-07-02 DE DE2431775A patent/DE2431775A1/de active Pending
- 1974-07-24 RO RO7400079581A patent/RO63973A/ro unknown
- 1974-07-25 NL NL7410033A patent/NL7410033A/xx unknown
- 1974-07-29 DD DD180187A patent/DD112759A5/xx unknown
- 1974-07-29 AR AR254925A patent/AR203854A1/es active
- 1974-07-31 AT AT627474A patent/AT337691B/de not_active IP Right Cessation
- 1974-08-01 JP JP49088635A patent/JPS5047978A/ja active Pending
- 1974-08-01 IT IT25881/74A patent/IT1049204B/it active
- 1974-08-01 BR BR6317/74A patent/BR7406317D0/pt unknown
- 1974-08-01 DK DK410874A patent/DK410874A/da unknown
- 1974-08-01 SE SE7409957A patent/SE7409957L/xx unknown
- 1974-08-02 FR FR7427017A patent/FR2240009A1/fr active Granted
- 1974-08-02 PL PL1974192766A patent/PL96805B1/pl unknown
- 1974-08-02 BE BE1006105A patent/BE818417A/xx unknown
- 1974-08-02 PL PL1974184214A patent/PL94238B1/pl unknown
- 1974-08-02 PL PL1974184215A patent/PL92429B1/pl unknown
- 1974-08-02 PL PL1974192765A patent/PL96804B1/pl unknown
- 1974-08-02 PL PL1974173196A patent/PL91696B1/pl unknown
- 1974-08-02 ES ES428914A patent/ES428914A0/es active Pending
-
1975
- 1975-01-01 AR AR257999A patent/AR205814A1/es active
- 1975-01-01 AR AR258000A patent/AR204130A1/es active
- 1975-09-04 SU SU7502170651A patent/SU565630A3/ru active
- 1975-09-12 SU SU7502171154A patent/SU582758A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| AR203854A1 (es) | 1975-10-31 |
| PL92429B1 (en, 2012) | 1977-04-30 |
| IL45073A0 (en) | 1974-09-10 |
| ZA743887B (en) | 1975-06-25 |
| DE2431775A1 (de) | 1975-02-20 |
| NL7410033A (nl) | 1975-02-04 |
| PL94238B1 (en, 2012) | 1977-07-30 |
| PL96805B1 (pl) | 1978-01-31 |
| BE818417A (fr) | 1975-02-03 |
| IT1049204B (it) | 1981-01-20 |
| BR7406317D0 (pt) | 1975-05-20 |
| JPS5047978A (en, 2012) | 1975-04-28 |
| FR2240009A1 (en) | 1975-03-07 |
| DD112759A5 (en, 2012) | 1975-05-05 |
| AR205814A1 (es) | 1976-06-07 |
| SU565630A3 (ru) | 1977-07-15 |
| ES428914A0 (es) | 1977-02-01 |
| AU7052874A (en) | 1976-01-08 |
| AR204130A1 (es) | 1975-11-20 |
| PL96804B1 (pl) | 1978-01-31 |
| AT337691B (de) | 1977-07-11 |
| ATA627474A (de) | 1976-11-15 |
| DK410874A (en, 2012) | 1975-04-01 |
| FR2240009B1 (en, 2012) | 1978-07-28 |
| RO63973A (fr) | 1978-09-15 |
| SE7409957L (en, 2012) | 1975-02-03 |
| IL45073A (en) | 1977-07-31 |
| SU582758A3 (ru) | 1977-11-30 |
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