OA10692A - Process for preparing dioxoazabicyclohexanes - Google Patents
Process for preparing dioxoazabicyclohexanes Download PDFInfo
- Publication number
- OA10692A OA10692A OA9800068A OA9800068A OA10692A OA 10692 A OA10692 A OA 10692A OA 9800068 A OA9800068 A OA 9800068A OA 9800068 A OA9800068 A OA 9800068A OA 10692 A OA10692 A OA 10692A
- Authority
- OA
- OAPI
- Prior art keywords
- process according
- base
- organic solvent
- formula
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- HGCBTXNRSHFSOF-UHFFFAOYSA-N 1-cyclohexylpiperidine-2,3-dione Chemical class O=C1C(=O)CCCN1C1CCCCC1 HGCBTXNRSHFSOF-UHFFFAOYSA-N 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 54
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 6
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 6
- 238000011084 recovery Methods 0.000 claims abstract description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 6
- 239000001488 sodium phosphate Substances 0.000 claims abstract description 6
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims abstract description 6
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims abstract description 6
- 235000019801 trisodium phosphate Nutrition 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 3
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- 229940093956 potassium carbonate Drugs 0.000 claims description 15
- 235000011181 potassium carbonates Nutrition 0.000 claims description 15
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000006386 neutralization reaction Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- CGKPGVZMSKVVOF-UHFFFAOYSA-N chloro(nitro)methane Chemical group [O-][N+](=O)CCl CGKPGVZMSKVVOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- -1 Ci-C6alkoxy Chemical group 0.000 claims 1
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
- 230000003019 stabilising effect Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 abstract 1
- 229910000024 caesium carbonate Inorganic materials 0.000 abstract 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002002 slurry Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- OTUKPXUUYJTFFJ-UHFFFAOYSA-N F.CC(C)=O Chemical compound F.CC(C)=O OTUKPXUUYJTFFJ-UHFFFAOYSA-N 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 101100074988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- ZIYVAZASIRJRHP-UHFFFAOYSA-N acetonitrile;hydron;fluoride Chemical compound F.CC#N ZIYVAZASIRJRHP-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- RAFKKJRZLDODKG-UHFFFAOYSA-N carbonic acid;propan-2-one Chemical compound CC(C)=O.OC(O)=O RAFKKJRZLDODKG-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9524466.1A GB9524466D0 (en) | 1995-11-30 | 1995-11-30 | Process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA10692A true OA10692A (en) | 2000-11-06 |
Family
ID=10784676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA9800068A OA10692A (en) | 1995-11-30 | 1998-05-29 | Process for preparing dioxoazabicyclohexanes |
Country Status (40)
| Country | Link |
|---|---|
| EP (1) | EP0863874B1 (fr) |
| JP (1) | JP2000507919A (fr) |
| KR (1) | KR100286157B1 (fr) |
| CN (1) | CN1203588A (fr) |
| AP (1) | AP746A (fr) |
| AR (1) | AR004766A1 (fr) |
| AT (1) | ATE198325T1 (fr) |
| AU (1) | AU707221B2 (fr) |
| BG (1) | BG102484A (fr) |
| BR (1) | BR9611833A (fr) |
| CA (1) | CA2231590A1 (fr) |
| CO (1) | CO4480102A1 (fr) |
| CZ (1) | CZ162298A3 (fr) |
| DE (1) | DE69611380T2 (fr) |
| DK (1) | DK0863874T3 (fr) |
| ES (1) | ES2152571T3 (fr) |
| GB (1) | GB9524466D0 (fr) |
| GR (1) | GR3035341T3 (fr) |
| HR (1) | HRP960555A2 (fr) |
| HU (1) | HUP9903571A3 (fr) |
| IL (1) | IL123561A0 (fr) |
| IS (1) | IS4707A (fr) |
| MA (1) | MA24015A1 (fr) |
| MX (1) | MX9804311A (fr) |
| MY (1) | MY132595A (fr) |
| NO (1) | NO982503D0 (fr) |
| NZ (1) | NZ321968A (fr) |
| OA (1) | OA10692A (fr) |
| PE (1) | PE24898A1 (fr) |
| PL (1) | PL326978A1 (fr) |
| PT (1) | PT863874E (fr) |
| RU (1) | RU2156238C2 (fr) |
| SK (1) | SK70798A3 (fr) |
| TN (1) | TNSN96145A1 (fr) |
| TR (1) | TR199800957T2 (fr) |
| TW (1) | TW401397B (fr) |
| UY (1) | UY24379A1 (fr) |
| WO (1) | WO1997019921A1 (fr) |
| YU (1) | YU63196A (fr) |
| ZA (1) | ZA9610053B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1087617A (ja) * | 1996-07-09 | 1998-04-07 | Pfizer Inc | キノリン系抗生物質の合成に有用な中間体の製法 |
| HN1998000106A (es) | 1997-08-01 | 1999-01-08 | Pfizer Prod Inc | Composiciones parenterales de alatroflaxacino |
| US7019142B2 (en) | 1998-01-16 | 2006-03-28 | Pfizer Inc. | Process for preparing naphthyridones and intermediates |
| WO2003081254A1 (fr) * | 2002-03-25 | 2003-10-02 | Council Of Scientific And Industrial Research | Profilage de proteines de plantes hyperacides |
| NL2000192C2 (nl) * | 2006-08-23 | 2008-02-26 | Veenvoort B V De | Stabiel bitumenschuim en de bereiding en het gebruik ervan. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5256791A (en) * | 1992-03-02 | 1993-10-26 | Pfizer Inc. | Preparation of intermediates in the synthesis of quinoline antibiotics |
| CZ286896B6 (en) * | 1994-01-18 | 2000-07-12 | Pfizer | Process for preparing pharmaceutically acceptable salts of naphthyridone carboxylic acid and intermediates for this preparation |
-
1995
- 1995-11-30 GB GBGB9524466.1A patent/GB9524466D0/en active Pending
-
1996
- 1996-10-21 TW TW085112856A patent/TW401397B/zh not_active IP Right Cessation
- 1996-10-31 AT AT96938058T patent/ATE198325T1/de not_active IP Right Cessation
- 1996-10-31 WO PCT/EP1996/004782 patent/WO1997019921A1/fr not_active Ceased
- 1996-10-31 JP JP9520100A patent/JP2000507919A/ja active Pending
- 1996-10-31 SK SK707-98A patent/SK70798A3/sk unknown
- 1996-10-31 TR TR1998/00957T patent/TR199800957T2/xx unknown
- 1996-10-31 DE DE69611380T patent/DE69611380T2/de not_active Expired - Fee Related
- 1996-10-31 EP EP96938058A patent/EP0863874B1/fr not_active Expired - Lifetime
- 1996-10-31 CN CN96198667A patent/CN1203588A/zh active Pending
- 1996-10-31 RU RU98112016/04A patent/RU2156238C2/ru active
- 1996-10-31 PL PL96326978A patent/PL326978A1/xx unknown
- 1996-10-31 BR BR9611833A patent/BR9611833A/pt not_active Application Discontinuation
- 1996-10-31 DK DK96938058T patent/DK0863874T3/da active
- 1996-10-31 IL IL12356196A patent/IL123561A0/xx unknown
- 1996-10-31 AU AU75629/96A patent/AU707221B2/en not_active Ceased
- 1996-10-31 ES ES96938058T patent/ES2152571T3/es not_active Expired - Lifetime
- 1996-10-31 CZ CZ981622A patent/CZ162298A3/cs unknown
- 1996-10-31 NZ NZ321968A patent/NZ321968A/xx unknown
- 1996-10-31 CA CA002231590A patent/CA2231590A1/fr not_active Abandoned
- 1996-10-31 PT PT96938058T patent/PT863874E/pt unknown
- 1996-10-31 HU HU9903571A patent/HUP9903571A3/hu unknown
- 1996-10-31 KR KR1019980703892A patent/KR100286157B1/ko not_active Expired - Fee Related
- 1996-11-21 HR HR9524466.1A patent/HRP960555A2/hr not_active Application Discontinuation
- 1996-11-27 TN TNTNSN96145A patent/TNSN96145A1/fr unknown
- 1996-11-27 MA MA24403A patent/MA24015A1/fr unknown
- 1996-11-27 UY UY24379A patent/UY24379A1/es not_active IP Right Cessation
- 1996-11-27 PE PE1996000850A patent/PE24898A1/es not_active Application Discontinuation
- 1996-11-27 AR ARP960105343A patent/AR004766A1/es unknown
- 1996-11-28 AP APAP/P/1996/000885A patent/AP746A/en active
- 1996-11-28 CO CO96062767A patent/CO4480102A1/es unknown
- 1996-11-28 YU YU63196A patent/YU63196A/sh unknown
- 1996-11-29 MY MYPI96005005A patent/MY132595A/en unknown
- 1996-11-29 ZA ZA9610053A patent/ZA9610053B/xx unknown
-
1998
- 1998-03-31 IS IS4707A patent/IS4707A/is unknown
- 1998-05-25 BG BG102484A patent/BG102484A/xx unknown
- 1998-05-29 OA OA9800068A patent/OA10692A/en unknown
- 1998-05-29 MX MX9804311A patent/MX9804311A/es unknown
- 1998-06-02 NO NO982503A patent/NO982503D0/no not_active Application Discontinuation
-
2001
- 2001-02-01 GR GR20010400166T patent/GR3035341T3/el not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO314456B1 (no) | Fremgangsmåter og mellomprodukter nyttige for å fremstille antifolater | |
| EP1767538A1 (fr) | Procédé pour la production d"un dérivé du 7alpha-méthoxy-3-chlorométhyle-1-oxacéphalosporine | |
| OA10692A (en) | Process for preparing dioxoazabicyclohexanes | |
| IL31082A (en) | Derivatives of heptenoic acid | |
| US5606072A (en) | Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehyde | |
| KR0141482B1 (ko) | 0-카르복시피리딜-및 0-카르복시퀴놀릴이미다졸리논의 개선된 제조방법 | |
| JPS61225183A (ja) | β−カルボリンの製造法 | |
| HUT70168A (en) | New process for producing imidazopyridine derivatives | |
| US5847158A (en) | Process for preparing 2,4-dioxo-3-azabicyclo 3.1.0!Hexanes | |
| JP3716434B2 (ja) | ２−置換−５−クロロイミダゾール | |
| JPH03130280A (ja) | ４―アリールオキシ―１，３―ベンゾジオキソール類の製造方法 | |
| SU1075676A1 (ru) | Способ получени тиазоло @ 3,4- @ 1,2,4 @ триазинов | |
| KR100201582B1 (ko) | 제초성 피리미딜옥시벤조산 옥심에스테르 유도체의제조방법 | |
| JPH04316531A (ja) | シクロヘキサノン誘導体 | |
| KR0181636B1 (ko) | 치환된 트리-6-히드록시 살리실리드 유도체 및 그의 제조방법 | |
| JP3110154B2 (ja) | ３（２ｈ）−ピリダジノン誘導体の製造方法 | |
| KR100212636B1 (ko) | 제초성 피리미딜옥시벤조산 옥심에스테르 유도체의 신규한 제조방법 | |
| JPS63280084A (ja) | １−アルキル−３−カルボキシ−４−シンノロン類の製造方法 | |
| JP2893906B2 (ja) | 不飽和ケトン化合物の製造方法 | |
| MXPA97005141A (en) | Procedure for preparing 2,4-dioxo-3-azabiciclo [3.1.0] hexa | |
| MXPA00002872A (en) | Processes and intermediates useful to make antifolates | |
| HU208679B (en) | Process for producing bicyclic azineacetic acid derivatives | |
| JPH04273860A (ja) | ３−カルボキシ−５−アシルオキシピラゾールの合成法 | |
| JPH07224043A (ja) | ヘキサヒドロピリダジンの製造法 | |
| HU188713B (en) | Process for preparing dihalo-vinyl-cyclopropane-carboxylic acids |